A photochemical approach to phenylalanines and related compounds by alkylation of glycine

Authors
Knowles, HS Hunt, K Parsons, AF
Citation
Hs. Knowles et al., A photochemical approach to phenylalanines and related compounds by alkylation of glycine, TETRAHEDRON, 57(38), 2001, pp. 8115-8124
Citations number
54
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
38
Year of publication
2001
Pages
8115 - 8124
Database
ISI
SICI code
0040-4020(20010917)57:38<8115:APATPA>2.0.ZU;2-1
Abstract
Phenylalanines can be prepared on UV photolysis of protected glycines in th e presence of di-tert-butyl peroxide, substituted toluenes and the photosen sitiser benzophenone. These reactions, which lead to highly selective mono- alkylation at the alpha -position of glycines, involve coupling of captodat ive alpha -glycine radicals with benzyl radicals. This method can be used t o selectively alkylate a variety of glycine derivatives using a range of su bstituted toluenes under neutral reaction conditions. (C) 2001 Elsevier Sci ence Ltd. All rights reserved.