Issue 24, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

Steven D. Bull,a   Stephen G. Davies,*a   A. Christopher Garnera  and  Michael D. O'Sheaa  

* Corresponding authors

a The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK
E-mail: steve.davies@chemistry.ox.ac.uk

Abstract

Addition of a range of organocuprates to (S)-N,N′-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2,5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-α-amino acids in excellent yield.

Graphical abstract: Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

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Article information

DOI
https://doi.org/10.1039/B108621A
Article type
Paper
Submitted
21 Sep 2001
Accepted
26 Oct 2001
First published
16 Nov 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 3281-3287

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Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

S. D. Bull, S. G. Davies, A. C. Garner and M. D. O'Shea, J. Chem. Soc., Perkin Trans. 1, 2001, 3281 DOI: 10.1039/B108621A

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