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Binaphthyl-Based Chiral Bifunctional Organocatalysts for Water Mediated Asymmetric List-Lerner-Barbas Aldol Reactions
Veeramanoharan Ashokkumar, Chinnadurai Chithirai kuma, Ayyanar Siva
Supramolecular and Organometallic Chemistry Lab, School of Chemistry, Madurai Kamaraj University,
Madurai 625 021, Tamil Nadu, India.
E-mail: [email protected]
Supporting Information
Table of Contents
S. NO Contents Page no.
1 NMR & Mass spectrum of intermediates, organocatatalysts 17, 18 and aldol products
2-25
2 HPLC chromatograms of aldol products 26-62
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2016
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Figure S1: 1H NMR Spectrum of compound 14.
Figure S2: 13C NMR Spectrum of compound 14.
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Figure S3: ESI-Mass Spectrum of compound 14.
Figure S4: 1H NMR Spectrum of compound 15.
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Figure S5: 13C NMR Spectrum of compound 15.
Figure S6: ESI-Mass Spectrum of compound 15.
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Figure S7: 1H NMR Spectrum of organocatalyst (17a).
Figure S8: 13C NMR Spectrum of organocatalyst (17a).
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Figure S9: ESI-Mass Spectrum of organocatalyst (17a).
Figure S10: 1H NMR Spectrum of organocatalyst (17b).
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Figure S11: 13C NMR Spectrum of organocatalyst (17b).
Figure S12: ESI-Mass Spectrum of organocatalyst (17b).
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Figure S13: 1H NMR Spectrum of aldol product 7a.
Figure S14: 13C NMR Spectrum of aldol product 7a.
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Figure S15: 1H NMR Spectrum of aldol product 7b.
Figure S16: 13C NMR Spectrum of aldol product 7b.
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Figure S17: 1H NMR Spectrum of aldol product 7c.
Figure S18: 13C NMR Spectrum of aldol product 7c.
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Figure S19: 1H NMR Spectrum of aldol product 7d.
Figure S20: 13C NMR Spectrum of aldol product 7d.
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Figure S21: 1H NMR Spectrum of aldol product 7e.
Figure S22: 13C NMR Spectrum of aldol product 7e.
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Figure S23: 1H NMR Spectrum of aldol product 7f.
Figure S24: 13C NMR Spectrum of aldol product 7f.
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Figure S25: 1H NMR Spectrum of aldol product 7g.
Figure S26: 13C NMR Spectrum of aldol product 7g.
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Figure S27: 1H NMR Spectrum of aldol product 7h.
Figure S28: 13C NMR Spectrum of aldol product 7h.
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Figure S29: 1H NMR Spectrum of aldol product 9a.
Figure S30: 13C NMR Spectrum of aldol product 9a.
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Figure S31: 1H NMR Spectrum of aldol product 9b.
Figure S32: 13C NMR Spectrum of aldol product 9b.
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Figure S33: 1H NMR Spectrum of aldol product 9c.
Figure S34: 13C NMR Spectrum of aldol product 9c.
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Figure S35: 1H NMR Spectrum of aldol product 10a.
Figure S36: 13C NMR Spectrum of aldol product 10a.
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Figure S37: 1H NMR Spectrum of aldol product 10b.
Figure S38: 13C NMR Spectrum of aldol product 10b.
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Figure S39: 1H NMR Spectrum of aldol product 10c.
Figure S40: 13C NMR Spectrum of aldol product 10c.
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Figure S41: 1H NMR Spectrum of aldol product 11a.
Figure S42: 13C NMR Spectrum of aldol product 11a.
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Figure S43: 1H NMR Spectrum of aldol product 11d.
Figure S44: 13C NMR Spectrum of aldol product 11d.
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Figure S45: 1H NMR Spectrum of aldol product 11e.
Figure S46: 13C NMR Spectrum of aldol product 11e.
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Figure S47: 1H NMR Spectrum of aldol product 11f.
Figure S48: 13C NMR Spectrum of aldol product 11f.
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Figure S49: HPLC chromatogram of (7) Racemic mixture.
Figure S50: HPLC chromatogram of (7a) in the presence organocatalyst (17a), CH3COOH
(2 mol%) and H2O in 0 °C condition.
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Figure S51: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S52: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and CH3OH in 0 °C condition.
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Figure S53: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and CH3CH2OH in 0 °C condition.
Figure S54: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and DMF in 0 °C condition.
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Figure S55: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and 1,4-Dioxane in 0 °C condition.
Figure S56: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and CH3OH + H2O in 0 °C condition.
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Figure S57: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and DMF + H2O in 0 °C condition.
Figure S58: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and 1,4-Dioxane + H2O in 0 °C condition.
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Figure S59: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S60: HPLC chromatogram of (7a) in the presence organocatalyst (17b), PhCOOH (2 mol%) and H2O in 0 °C condition.
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Figure S61: HPLC chromatogram of (7a) in the presence organocatalyst (17b), PhCOOH (10 mol%) and H2O in 0 °C condition.
Figure S62: HPLC chromatogram of (7a) in the presence organocatalyst (17b), HCOOH (2 mol%) and H2O in 0 °C condition.
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Figure S63: HPLC chromatogram of (7a) in the presence organocatalyst (17b), HCOOH (10 mol%) and H2O in 0 °C condition.
Figure S64: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S65: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (10 mol%) and H2O in 0 °C condition.
Figure S66: HPLC chromatogram of (7a) in the presence organocatalyst (17b), Oxalic acid (2 mol%) and H2O in 0 °C condition.
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Figure S67: HPLC chromatogram of (7a) in the presence organocatalyst (17b), Oxalic acid (10 mol%) and H2O in 0 °C condition.
Figure S68: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 1 mol%), CH3COOH (2 mol%) and H2O in 30 °C condition.
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Figure S69: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 1 mol%), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S70: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 1 mol%), CH3COOH (2 mol%) and H2O in 60 °C condition.
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Figure S71: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 1 mol%), CH3COOH (2 mol%) and H2O in −20 °C condition.
Figure S72: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 5 mol%), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S73: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 10 mol%), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S74: HPLC chromatogram of (7a) in the presence organocatalyst (17b, 20 mol%), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S75: HPLC chromatogram of (7a) Racemic mixture.
Figure S76: HPLC chromatogram of (7a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S77: HPLC chromatogram of (8a) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S78: HPLC chromatogram of (7b) Racemic mixture.
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Figure S79: HPLC chromatogram of (7b) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S80: HPLC chromatogram of (8b) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S81: HPLC chromatogram of (7c) Racemic mixture.
Figure S82: HPLC chromatogram of (7c) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S83: HPLC chromatogram of (8c) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S84: HPLC chromatogram of (7d) Racemic mixture.
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Figure S85: HPLC chromatogram of (7d) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S86: HPLC chromatogram of (8d) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S87: HPLC chromatogram of (7e) in the presence organocatalyst (17b), CH3COOH (2 mole%) and H2O in 0 °C conditions.
Figure S88: HPLC chromatogram of (8e) in the presence organocatalyst (18b), CH3COOH
(2 mol%) and H2O in 0 °C condition.
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Figure S89: HPLC chromatogram of (7f) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S90: HPLC chromatogram of (8f) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S91: HPLC chromatogram of (7g) Racemic mixture.
Figure S92: HPLC chromatogram of (7g) in the presence organocatalyst (17b), CH3COOH
(2 mol%) and H2O in 0 °C condition.
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Figure S93: HPLC chromatogram of (8g) in the presence organocatalyst (18b), CH3COOH
(2 mol%) and H2O in 0 °C condition.
Figure S94: HPLC chromatogram of (7h) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S95: HPLC chromatogram of (8h) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S96: HPLC chromatogram of (9a) Racemic mixture.
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Figure S97: HPLC chromatogram of (9a) in the presence organocatalyst (17a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S98: HPLC chromatogram of (9a) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S99: HPLC chromatogram of (9b) Racemic mixture.
Figure S100: HPLC chromatogram of (9b) in the presence organocatalyst (17a), CH3COOH
(2 mol%) and H2O in 0 °C condition.
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Figure S101: HPLC chromatogram of (9b) in the presence organocatalyst (17b), CH3COOH
(2 mol%) and H2O in 0 °C condition.
Figure S102: HPLC chromatogram of (9c) Racemic mixture.
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Figure S103: HPLC chromatogram of (9c) in the presence organocatalyst (17a), CH3COOH
(2 mol%) and H2O in 0 °C condition.
Figure S104: HPLC chromatogram of (9c) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S105: HPLC chromatogram of (10a) in the presence organocatalyst (17a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S106: HPLC chromatogram of (10a) in the presence organocatalyst (17b),
CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S107: HPLC chromatogram of (10b) in the presence organocatalyst (17a),
CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S108: HPLC chromatogram of (10b) in the presence organocatalyst (17b),
CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S109: HPLC chromatogram of (10c) in the presence organocatalyst (17a), CH3COOH
(2 mol%) and H2O in 0 °C condition.
Figure S110: HPLC chromatogram of (10c) in the presence organocatalyst (17b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S111: HPLC chromatogram of (11a) in the presence organocatalyst (17a), CH3COOH
(2 mol%) and H2O in 0 °C condition.
Figure S112: HPLC chromatogram of (11a) in the presence organocatalyst (17b),CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S113: HPLC chromatogram of (12a) in the presence organocatalyst (18a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S114: HPLC chromatogram of (12a) in the presence organocatalyst (18b),
CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S115: HPLC chromatogram of (11d) in the presence organocatalyst (18a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S116: HPLC chromatogram of (11d) in the presence organocatalyst (18b), CH3COOH (2
mol%) and H2O in 0 °C condition.
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Figure S114: HPLC chromatogram of (11e) in the presence organocatalyst (18a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S118: HPLC chromatogram of (11e) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.
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Figure S119: HPLC chromatogram of (11f) in the presence organocatalyst (17a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S120: HPLC chromatogram of (11f) in the presence organocatalyst (17b), CH3COOH
(2 mol%) and H2O in 0 °C condition.
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Figure S121: HPLC chromatogram of (12f) in the presence organocatalyst (18a), CH3COOH (2 mol%) and H2O in 0 °C condition.
Figure S122: HPLC chromatogram of (12f) in the presence organocatalyst (18b), CH3COOH (2 mol%) and H2O in 0 °C condition.