Thomas, Achamma ; Manjunatha, Sulur G. ; Rajappa, Srinivasachari (1992) Synthesis of dipeptides via addition of N-(nitroacetyl)amino-acid derivatives to Michael acceptors: scope, stereoselectivity, and absolute configuration Helvetica Chimica Acta, 75 (3). pp. 715-720. ISSN 0018-019X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/hlca.19...
Related URL: http://dx.doi.org/10.1002/hlca.19920750306
Abstract
Michael addition of N-nitroacetyl derivatives 1 of proline esters using KF under phase-transfer catalysis resulted in the formation of adducts 3-9 with chemical yields ranging from 40-90% (Scheme). Stereoselectivity of up to 51% was obtained on addition of benzyl N-(nitroacetyl)-L-prolinate (1a). The absolute configuration at the newly created chiral centre was established in the case of 9 by carrying out a reductive acylation and comparing the product 10 with an authentic sample of ethyl N-(O5-ethyl N2-acetyl-L-glutam-1-yl)-L-prolinate (L, L-10).
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley and Sons. |
ID Code: | 50341 |
Deposited On: | 23 Jul 2011 07:19 |
Last Modified: | 23 Jul 2011 07:19 |
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