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Asymmetric Aldol Reaction of Chloral Catalyzed by Diarylprolinol
Author(s) -
Hayashi Yujiro,
Watanabe Shoya,
Yasui Yusuke,
Umemiya Shigenobu
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500282
Subject(s) - aldol reaction , chloral hydrate , aldehyde , chemistry , chloral , catalysis , organic chemistry , hydrate , enantioselective synthesis , trifluoromethyl , psychology , psychiatry , alkyl
The asymmetric cross‐aldol reaction of chloral hydrate with aldehyde pronucleophiles catalyzed by a trifluoromethyl‐substituted diarylprolinol was accomplished to afford γ‐trichloro‐β‐hydroxy aldehydes in good yields with excellent enantioselectivities. The resulting aldehyde products were converted into chiral α‐azido, α‐(4‐methyl)phenoxy, and α‐fluoro esters without a loss in the diastereo‐ or enantioselectivities.