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Palladium on Charcoal plus Enantiopure Amino Alcohols as Catalytic Systems for the Enantioselective 1,4‐Reduction of α‐Substituted α,β‐Unsaturated Ketones
Author(s) -
Thorey Claire,
Bouquillon Sandrine,
Helimi Abdellatif,
Hénin Françoise,
Muzart Jacques
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200207)2002:13<2151::aid-ejoc2151>3.0.co;2-y
Subject(s) - enantiopure drug , chemistry , enantioselective synthesis , catalysis , palladium , protonation , double bond , organic chemistry , ketone , hydrogen , alcohol , medicinal chemistry , ion
The chemoselective reduction of α,β‐unsaturated cyclic ketones 1−7 to the corresponding saturated ketones 8−12 was shown to proceed mainly by 1,4‐addition of hydrogen to the activated double bond, resulting in enolic species. These entities could be selectively protonated in the presence of enantiopure amino alcohols to afford the corresponding saturated ketones with ee values of up to 47%. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)