Issue 18, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

1,4-Asymmetric reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group

Shuichi Nakamura,a   Masayuki Kuroyanagi,a   Yoshihiko Watanabea  and  Takeshi Torua  

a Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan

Abstract

Reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group with DIBAL gives γ-hydroxy sulfoxides with high stereoselectivity in the ratio 95∶5. In comparison with the lower stereoselectivities obtained in the reaction of γ-keto sulfoxides bearing p-tolyl or 2,4,6-trimethylphenyl groups, the sterically bulky (2,4,6-triisopropylphenyl)sulfinyl group is extremely efficient in effecting high 1,4-remote asymmetric induction.

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Article information

DOI
https://doi.org/10.1039/B004782L
Article type
Paper
Submitted
14 Jun 2000
Accepted
31 Jul 2000
First published
06 Sep 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3143-3148

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1,4-Asymmetric reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group

S. Nakamura, M. Kuroyanagi, Y. Watanabe and T. Toru, J. Chem. Soc., Perkin Trans. 1, 2000, 3143 DOI: 10.1039/B004782L

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