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1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) Catalyzed Regiospecific and Diastereoselective Reaction of Chiral N ‐( tert ‐Butanesulfinyl)ketimines and α , β ‐Unsaturated Trifluoromethyl Ketones
Author(s) -
Zhang Fan,
Liu Zhenjiang,
Liu Jintao
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100133
Subject(s) - chemistry , trifluoromethyl , catalysis , medicinal chemistry , ene reaction , organic chemistry , alkyl
The reaction of chiral N ‐( tert ‐butanesulfinyl)ketimines and α , β ‐unsaturated trifluoromethyl ketones catalyzed by DBU was achieved under mild conditions. 1,2‐Addition products, precursors of chiral trifluoromethylated 1,3‐amino alcohols, were obtained diastereoselectively ( dr value up to 95:5) in moderate yields (up to 76%). A possible catalytic cycle was proposed.