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Straightforward Synthesis of Diverse 1‐Deoxyazapyranosides via Stereocontrolled Nucleophilic Additions to Six‐Membered Cyclic Nitrones
Author(s) -
Chan TingHao,
Chang YiFan,
Hsu JungJung,
Cheng WeiChieh
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001045
Subject(s) - stereocenter , chemistry , nucleophilic addition , nucleophile , reagent , chiral auxiliary , grignard reagent , enantioselective synthesis , stereochemistry , grignard reaction , combinatorial chemistry , organic chemistry , catalysis
A systematic study of diastereoselective nucleophilic addition of Grignard reagents to six‐membered chiral tri‐ O ‐benzyl cyclic nitrones is described. With all eight chiral cyclic nitrones and asymmetric reaction conditions in hand, a practical methodology is established for the preparation of diverse 1‐deoxyazapyranosides bearing various stereogenic centers.