Issue 16, 2004
From the journal:

Chemical Communications

N-Allyl-N-tert-butyldimethylsilylamine for chiral ligand-controlled asymmetric conjugate addition to tert-butyl alkenoates†

Hirohisa Doi,a   Takeo Sakai,a   Ken-ichi Yamadaa  and  Kiyoshi Tomioka*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Kyoto 606-8501, Japan
E-mail: tomioka@pharm.kyoto-u.ac.jp
Fax: +81-75-753-4604
Tel: +81-75-753-4553

Abstract

The chiral ligand controlled asymmetric conjugate addition reaction of lithium N-allyl-N-(tert-butyldimethylsilyl)amide to alkenoates proceeded smoothly to give, after protodesilylation, the corresponding 3-allylaminoalkanoates with high enantioselectivities in high yields. The allyl group on the nitrogen atom was easily removable to afford 3-aminoalkanoates.

Graphical abstract: N-Allyl-N-tert-butyldimethylsilylamine for chiral ligand-controlled asymmetric conjugate addition to tert-butyl alkenoates

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Article information

DOI
https://doi.org/10.1039/B405347H
Article type
Communication
Submitted
08 Apr 2004
Accepted
26 May 2004
First published
30 Jun 2004

Chem. Commun., 2004, 1850-1851

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N-Allyl-N-tert-butyldimethylsilylamine for chiral ligand-controlled asymmetric conjugate addition to tert-butyl alkenoates

H. Doi, T. Sakai, K. Yamada and K. Tomioka, Chem. Commun., 2004, 1850 DOI: 10.1039/B405347H

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