cheminform abstract: regioselective, borinic acid-catalyzed monoacylation, sulfonylation and...

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ChemInform 2012, 43, issue 01 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Protection O 0345 DOI: 10.1002/chin.201239044 Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkyla- tion of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies. — The method can be generally applied to the monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups. In addition, 1,2- and 1,3-diols not derived from carbohydrates are selectively tosylated, alkylated, and acylated. Compe- tition experiments, kinetic studies, and computational modeling are made to propose a reaction mechanism. — (LEE, D.; WILLIAMSON, C. L.; CHAN, L.; TAYLOR*, M. S.; J. Am. Chem. Soc. 134 (2012) 19, 8260-8267, http://dx.doi.org/10.1021/ja302549c ; Dep. Chem., Univ. Toronto, Toronto, Ont. M5S 3H6, Can.; Eng.) — Klein 39- 044

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Page 1: ChemInform Abstract: Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies

ProtectionO 0345 DOI: 10.1002/chin.201239044

Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkyla-tion of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies. — The method can be generally applied to the monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups. In addition, 1,2- and 1,3-diols not derived from carbohydrates are selectively tosylated, alkylated, and acylated. Compe-tition experiments, kinetic studies, and computational modeling are made to propose a reaction mechanism. — (LEE, D.; WILLIAMSON, C. L.; CHAN, L.; TAYLOR*, M. S.; J. Am. Chem. Soc. 134 (2012) 19, 8260-8267, http://dx.doi.org/10.1021/ja302549c ; Dep. Chem., Univ. Toronto, Toronto, Ont. M5S 3H6, Can.; Eng.) — Klein

39- 044

ChemInform 2012, 43, issue 01 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Page 2: ChemInform Abstract: Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies

ChemInform 2012, 43, issue 01 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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