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β‐Siloxy‐α‐haloketones through Highly Diastereoselective Single and Double Mukaiyama Aldol Reactions
Author(s) -
Saadi Jakub,
Yamamoto Hisashi
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204493
Subject(s) - aldol reaction , polyketide , silylation , chemistry , computer science , world wide web , organic chemistry , biosynthesis , enzyme , catalysis
Double‐action haloketones : A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α‐chloro‐ and α‐fluoroketones with a wide range of aldehydes, providing anti ‐β‐siloxy‐α‐haloketones. This process is compatible with one‐pot double‐aldol methodology and allows for rapid access to new halogen‐modified polyketide fragments bearing up to four contiguous stereocenters (see scheme).