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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.
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Nicolaou et al. (2002) studied this question.
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