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Highly Diastereoselective Oxy‐Michael Additions of Enantiopure δ‐Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2‐Amino Alcohols
Author(s) -
Adderley Nicola J.,
Buchanan David J.,
Dixon Darren J.,
Lainé Dramane I.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352007
Subject(s) - enantiopure drug , lactol , michael reaction , chemistry , organic chemistry , enantioselective synthesis , lactone , catalysis
The “naked” alkoxide 1 of ( S )‐6‐methyl‐δ‐lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy‐Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2‐amino alcohol products. R 1 =alkyl, aryl, furanyl, thiophenyl; R 2 ,R 3 =(CH 2 ) 3 CHCH 3 O.