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A Novel Regio‐ and Stereoselective Synthesis of Sulfamidates from 1,2‐Diols Using Burgess and Related Reagents: A Facile Entry into β ‐Amino Alcohols
Author(s) -
Nicolaou K. C.,
Huang Xianhai,
Snyder Scott A.,
Bheema Rao Paraselli,
Bella Marco,
Reddy Mali V.
Publication year - 2002
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 - 10.1002/1521-3773(20020301)41:5<834::aid-anie834>3.0.co;2-v
Subject(s) - enantiopure drug , stereoselectivity , reagent , amino acid , chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , biochemistry
An increasingly targeted functional motif in organic synthesis is the ubiquitous chiral β ‐amino alcohol. A novel two‐step approach for the regio‐ and stereoselective synthesis of a wide variety of 1,2‐amino alcohols 4 involves the initial construction of chiral sulfamidates 3 from enantiopure diols 1 , mediated by Burgess reagent ( 2 , R = Me), followed by mild treatment with aqueous acid. Furthermore, the development of several new Burgess‐type reagents 2 (R = CH 2 Ph, CH 2 ‐ o ‐NO 2 Ph, CH 2 CH=CH 2 , CH 2 CCl 3 ) greatly extends the applications of this protocol.