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Updated: Jun 13, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Mukaiyama aldol addition to alpha-chloro-substituted aldehydes. Origin of the unexpected syn selectivity
Tessie Borg1, Jakob Danielsson, Peter Somfai
1Organic Chemistry, KTH Chemical Science and Engineering, Royal Institute of Technology, 100 44 Stockholm, Sweden.
Abstract:
The addition of sterically demanding enolsilanes to alpha-chloro aldehydes results unexpectedly in preferential formation of the anti-PFA product (1,2-syn), while the addition of the corresponding boron enolate furnishes the expected polar Felkin-Anh product (1,2-anti). A stereoinduction model explaining these observations is proposed.
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