Callebaut, Gert and Mangelinckx, Sven and Kiss, Loránd and Sillanpää, Reijo and Fülöp, Ferenc and De Kimpe, Norbert (2012) Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro- N-sulfinylimines. Organic and Biomolecular Chemistry, 10. pp. 2326-2338. ISSN 1477-0520, ESSN: 1477-0539
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Abstract
The efficient asymmetric synthesis of new chiral γ-chloro-α,β-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral α-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity of the Mannich-type reaction. The γ-chloro-α,β-diamino acid derivatives proved to be excellent building blocks for ring closure towards optically pure anti- and syn-β,γ-aziridino-α-amino esters, and subsequent ring transformation into trans-3-aminoazetidine-2-carboxylic acid derivatives and α,β-diamino- γ-butyrolactones.
Item Type: | Article |
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Subjects: | Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia |
Depositing User: | Dr Loránd Kiss |
Date Deposited: | 30 Dec 2015 19:55 |
Last Modified: | 30 Dec 2015 19:55 |
URI: | http://real.mtak.hu/id/eprint/31587 |
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