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Issue 24, 2001
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Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

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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


Submitted
21 Sep 2001
Accepted
26 Oct 2001
First published
16 Nov 2001

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

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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