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Synthesis 2015; 47(05): 679-691
DOI: 10.1055/s-0034-1378943
DOI: 10.1055/s-0034-1378943
paper
Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines
Further Information
Publication History
Received: 01 September 2014
Accepted after revision: 06 November 2014
Publication Date:
10 December 2014 (online)
Abstract
Nine R/S pairs of 2-heteroaromatic-substituted 1,2-amino alcohols were synthesized through 1,2-nucleophilic addition between chiral N-(tert-butylsulfinyl)imines and heteroaromatic carbanions. In most cases, the R S-isomer of N-(tert-butylsulfinyl)imines afforded the R amino alcohol from deprotection of the major diastereomer, and S S-imines afforded the S product. In general, this procedure allows for the preparation of a variety of enantiomeric pairs of 2-heteroaromatic-substituted 1,2-amino alcohols on a practical scale (>10 g) in two steps in good yields.
Key words
amino alcohols - asymmetric synthesis - chiral auxiliaries - heterocycles - stereoselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378943.
- Supporting Information
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