Highly Diastereoselective Oxy‐Michael Additions of Enantiopure δ‐Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2‐Amino Alcohols | Zendy

Adderley Nicola J. | Zendy; Buchanan David J. | Zendy; Dixon Darren J. | Zendy; Lainé Dramane I. | Zendy

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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.

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