Synthesis 2015; 47(05): 679-691
DOI: 10.1055/s-0034-1378943
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

Yantao Chen*
a  AstraZeneca Innovative Medicines Cardiovascular and Metabolic Diseases, 431 83 Mölndal, Sweden   Email: yantao.chen@astrazeneca.com
,
Frederick W. Goldberg
b  AstraZeneca Innovative Medicines Oncology, Alderley Park, Macclesfield, Cheshire, SK10 4TG, UK
,
Jian Xiong
c  WuXi AppTec (Shanghai) Co., Ltd., No. 1 Building, #288 FuTe ZhongLu, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. of China
,
Shujun Wang
c  WuXi AppTec (Shanghai) Co., Ltd., No. 1 Building, #288 FuTe ZhongLu, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 01 September 2014

Accepted after revision: 06 November 2014

Publication Date:
10 December 2014 (eFirst)

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.

Supporting Information

 
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