652140-58-4Relevant articles and documents
Asymmetric synthesis of substituted 1-aminocyclopropane1-carboxylic acids via diketopiperazine methodology
Bunuel, Elena,Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,Savory, Edward D.,Smith, Andrew D.,Vickers, Richard J.,Watkin, David J.
, p. 2531 - 2542 (2007/10/03)
Diketopiperazinespirocyclopropane 12 is prepared in > 98% d.e. via the conjugate addition of a phosphorus ylide to (6S)-N, N′-bis(p-methoxybenzyl)-3-methylenepiperazine-2,5-dione 2. Deprotection and hydrolysis of adduct 12 and subsequent peptide coupling demonstrate the applicability of this methodology to the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acids for incorporation into novel peptides. A model for the high level of diastereofacial selectivity observed in the cyclopropanation reaction is presented. A highly selective asymmetric approach (> 98% d.e.) to (S)-[2,2-2H 2]-1-aminocyclopropane-l-carboxylic acid 29 is also reported via a deuterated sulfur ylide addition to acceptor 2.
