Mukaiyama aldol addition to alpha-chloro-substituted aldehydes. Origin of the unexpected syn selectivity

作者:Borg Tessie; Danielsson Jakob; Somfai Peter*
来源:Chemical Communications, 2010, 46(8): 1281-1283.
DOI:10.1039/b922954j

摘要

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.

  • 出版日期2010