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Synthesis of Vicinal Aminoalcohols by Stereoselective Aza‐Wacker Cyclizations: Access to (−)‐Acosamine by Redox Relay
Author(s) -
Weinstein Adam B.,
Schuman David P.,
Tan Zhi Xu,
Stahl Shan S.
Publication year - 2013
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.201305926
Subject(s) - chemistry , library science , computer science
Diastereoselective aza‐Wacker cyclization of O ‐allyl hemiaminals under aerobic conditions enables efficient access to 1,2‐aminoalcohol derivatives from allylic alcohols. The scope of this method is presented and its utility is highlighted in a streamlined synthesis of the biologically important aminosugar (−)‐acosamine. Cbz=benzyloxycarbonyl, TBDPS= tert ‐butyldiphenylsilyl, TBS= tert ‐butyldimethylsilyl.