Issue 19, 2011
From the journal:

Organic & Biomolecular Chemistry

Practical and stereoselective synthesis of β-amino sulfones from alkyl phenyl sulfones and N-(tert-butylsulfinyl) aldimines†

Hua Zhang,ab   Ya Li,b   Wei Xu,c   Wenrui Zheng,b   Pei Zhou*d  and  Zhihua Sun*b  

* Corresponding authors

a School of Environment Science and Engineering, Shanghai Jiaotong University, Shanghai, China

b College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, China
E-mail: sungaris@gmail.com
Fax: +86 21 6779 1432
Tel: +86 21 6779 1432

c Department of Biology, Texas A&M University, College Station, Texas, USA

d Key Laboratory of Urban Agriculture (South), School of Agriculture College and Biology, Ministry of Agriculture, Shanghai Jiaotong University, Shanghai, China
E-mail: peizhousjtu@163.com
Fax: +86 21 3420 5762
Tel: +86 21 3420 5762

Abstract

A practical and straightforward approach for the highly stereoselective synthesis of β-amino sulfones was developed. With lithium bis(trimethylsilyl)amide as the base, the corresponding sulfone-stabilized carbanion derived from alkylphenyl sulfone can be transferred to N-(tert-butylsulfinyl) aldimines in excellent yields and with high diastereoselectivity.

Graphical abstract: Practical and stereoselective synthesis of β-amino sulfones from alkyl phenyl sulfones and N-(tert-butylsulfinyl) aldimines

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Article information

DOI
https://doi.org/10.1039/C1OB05992K
Article type
Communication
Submitted
20 Jun 2011
Accepted
01 Aug 2011
First published
02 Aug 2011

Org. Biomol. Chem., 2011,9, 6502-6505

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Practical and stereoselective synthesis of β-amino sulfones from alkyl phenyl sulfones and N-(tert-butylsulfinyl) aldimines

H. Zhang, Y. Li, W. Xu, W. Zheng, P. Zhou and Z. Sun, Org. Biomol. Chem., 2011, 9, 6502 DOI: 10.1039/C1OB05992K

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