A Novel Regio- and Stereoselective Synthesis of Sulfamidates from 1,2-Diols Using Burgess and Related Reagents: A Facile Entry into β-Amino Alcohols We thank Professor K. Barry Sharpless for the gracious donation of several of the starting diol substrates. We also thank Drs. D. H. Huang, G. Suizdak, and R. Chadja for NMR spectroscopic, mass spectrometric, and X-ray crystallographic assistance, respectively. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, predoctoral fellowships from the National Science Foundation and Pfizer (S.A.S.), a postdoctoral fellowship from The Skaggs Institute for Chemical Biology (X.H.), and grants from American Biosciences, Amgen, Array Biopharma, Boehringer-Ingelheim, Glaxo, Hoffman-LaRoche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

Abstract

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.