Diastereoselective synthesis of 4-substituted l-prolines by intramolecular radical cyclization of N-aryl sulphonyl-N-allyl 3-bromoalanines: interesting dependence of selectivity on the nature of sulphonamido groups

Basak, Amit ; Bag, Subhendu Sekhar ; Rudra, Kakali Rani ; Barman, Jharna ; Dutta, Sumana (2002) Diastereoselective synthesis of 4-substituted l-prolines by intramolecular radical cyclization of N-aryl sulphonyl-N-allyl 3-bromoalanines: interesting dependence of selectivity on the nature of sulphonamido groups Chemistry Letters, 31 (7). p. 710. ISSN 0366-7022

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Official URL: http://joi.jlc.jst.go.jp/JST.JSTAGE/cl/2002.710?fr...

Related URL: http://dx.doi.org/10.1246/cl.2002.710

Abstract

Enantiopure 4-substituted L-proline derivatives have been prepared via intramolecular radical cyclization of N-aryl sulphonyl-N-allyl-3-bromo-L-alanines in high yields. Surprisingly, the extent of selectivity was found to be primarily dependent on the nature of sulphonamido aryl group and could be as high as 33:1 using naphthyl sulphonamide.

Item Type:Article
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