A Novel Regio- and Stereoselective Synthesis of Sulfamidates from 1,2-Diols Using Burgess and Related Reagents: A Facile Entry into β-Amino Alcohols

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...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2002-03, Vol.41 (5), p.834-838
Main Authors: Nicolaou, K. C., Huang, Xianhai, Snyder, Scott A., Bheema Rao, Paraselli, Bella, Marco, Reddy, Mali V.
Format: Article
Language:English
Subjects:
amino alcohols
asymmetric synthesis
Burgess reagents
sulfamidates
synthetic methods
Online Access:Get full text
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Summary: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 = CH2Ph, CH2‐o‐NO2Ph, CH2CH=CH2, CH2CCl3) greatly extends the applications of this protocol.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020301)41:5<834::AID-ANIE834>3.0.CO;2-V