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Enantioselective Synthesis of Vicinal Amino Alcohols by Oxa‐Michael Addition of (−)‐ N ‐Formylnorephedrine to Nitroalkenes
Author(s) -
Enders Dieter,
Haertwig Andreas,
Raabe Gerhard,
Runsink Jan
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199623881
Subject(s) - enantioselective synthesis , vicinal , michael reaction , enantiomer , nucleophile , chemistry , adduct , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
The asymmetric oxa‐Michael addition of (‐)‐ N ‐formylnorephedrine, a chiral oxygen nucleophile with a removable auxiliary, to ( E )‐nitroalkenes 1 permits the enantioselective synthesis of protected vicinal amino alcohols ( R )‐ 3 with high enantiomeric excesses after reduction of the 1,4‐adducts 2 . This new procedure opens an efficient entry to synthetic building blocks for natural products and drugs.