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Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

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posted on 15.03.2013, 00:00 by P. Veeraraghavan Ramachandran, Daniel Nicponski, Bomi Kim
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 an aldol reaction in the presence of a phosphine–borane adduct is also reported.