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Asymmetric Tandem Wittig Rearrangement/Mannich Reactions
Author(s) -
Giampietro Natalie C.,
Wolfe John P.
Publication year - 2010
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.201000609
Subject(s) - chemistry , stereoselectivity , wittig reaction , tandem , alcohol , cleavage (geology) , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , materials science , geotechnical engineering , fracture (geology) , engineering , composite material
The choice is yours : A highly stereoselective synthesis of α‐alkyl‐α‐hydroxy‐β‐amino esters is accomplished through a tandem Wittig‐rearrangement/Mannich reaction sequence. Transformations of N ‐benzyl or N ‐Boc imines proceed with high selectivity for formation of syn ‐amino alcohol derivatives, whereas N ‐Boc‐2‐(phenylsulfonyl)amines generate anti ‐amino alcohol products. Auxiliary cleavage (transesterification or reduction) yields enantiomerically enriched products with up to 96 % ee.