STEREOSELECTIVE ALDOL REACTIONS OF β-BORONATE CARBONYL DERIVATIVES.

Article abstract of DOI:10.1016/0040-4039(91)80370-L

Deprotonation of β-boronate carbonyl derivatives can be readily achieved using LDA.Reaction of the resulting enolates with aldehydes gives the corresponding Aldol products, with high syn-selectivity for Z-enolates.This result is consistent with chelation enhanced stabilisation of the enolate geometry via the boronate moiety.