Organic letters

Total Regio-and Diastereocontrol in the Aldol Reactions of Dienolborinates

PV Ramachandran, D Nicponski, B Kim

Index: Ramachandran, P. Veeraraghavan; Nicponski, Daniel; Kim, Bomi Organic Letters, 2013 , vol. 15, # 6 p. 1398 - 1401

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Citation Number: 9

Abstract

It is reported that appropriate dienolborinates can provide access to both diastereomers of 2- (hydroxymethyl) but-3-enoates through exclusive α-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of ...