Issue 10, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Indium-mediated diastereoselective allylation reactions: preparation of α-hydroxy and α-amino acids

Jung Gyu Lee,ab   Kyung Il Choi,a   Ae Nim Pae,a   Hun Yeong Koh,a   Yonghan Kangb  and  Yong Seo Cho*a  

* Corresponding authors

a Biochemicals Research Center, Korea Institute of Science and Technology, Cheongryang P.O. Box 131, Seoul 130-650, Korea
E-mail: ys4049@kist.re.kr
Fax: +82-2-958-5189

b Department of Chemistry College of Sciences, Hanyang University, 1271 Sa-1-dong, Ansan city, Kyunggi-do 425-791, Korea

Abstract

The hemiacetals of (+)- and (−)-N-glyoxyloylbornane-10,2-sultam and their imines reacted with allyl iodide in the presence of indium in DMF to give the corresponding α-hydroxy and α-amino camphor sultam derivatives with high diastereoselectivities (86–90% de). This method could be useful for preparation of α-hydroxy and α-amino acids.

Graphical abstract: Indium-mediated diastereoselective allylation reactions: preparation of α-hydroxy and α-amino acids

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Article information

DOI
https://doi.org/10.1039/B110505C
Article type
Paper
Submitted
15 Nov 2001
Accepted
12 Mar 2002
First published
04 Apr 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1314-1317

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Indium-mediated diastereoselective allylation reactions: preparation of α-hydroxy and α-amino acids

J. Gyu Lee, K. I. Choi, A. N. Pae, H. Y. Koh, Y. Kang and Y. S. Cho, J. Chem. Soc., Perkin Trans. 1, 2002, 1314 DOI: 10.1039/B110505C

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