title: Total regio- and diastereocontrol in the aldol reactions of dienolborinates.
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 an aldol reaction in the presence of a phosphine-borane adduct is also reported.
authors: Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu
authors: P Veeraraghavan
authors: PV
authors: Ramachandran
authors: Daniel
authors: D
authors: Nicponski
authors: Bomi
authors: B
authors: Kim