MEMORY EFFECT OF CHIRALITY IN THE PHOTOCYCLIZATION OF MODIFIED DIPEPTIDES

Authors
SAUER S SCHUMACHER A BARBOSA F GIESE B
Citation
S. Sauer et al., MEMORY EFFECT OF CHIRALITY IN THE PHOTOCYCLIZATION OF MODIFIED DIPEPTIDES, Tetrahedron letters, 39(22), 1998, pp. 3685-3688
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
22
Year of publication
1998
Pages
3685 - 3688
Database
ISI
SICI code
0040-4039(1998)39:22<3685:MEOCIT>2.0.ZU;2-2
Abstract
Photocyclizations of dipeptides 5 and 8 occur mainly with retention of configuration at the stereogenic center of alanine. This memory effec t of chirality is explained by a hindered rotation in the two intermed iate biradicals 9 and 10 that slows down the equilibration of the radi cals. (C) 1998 Elsevier Science Ltd. All rights reserved.