SELECTIVE FORMATION OF 1-AZETINE DERIVATIVES VIA 1,3-PHOTOACYL MIGRATION OF SUBSTITUTED ALPHA-DEHYDROPHENYLALANINES

Authors
KUBO K KOSHIBA M HOSHINA H SAKURAI T
Citation
K. Kubo et al., SELECTIVE FORMATION OF 1-AZETINE DERIVATIVES VIA 1,3-PHOTOACYL MIGRATION OF SUBSTITUTED ALPHA-DEHYDROPHENYLALANINES, Heterocycles, 48(1), 1998, pp. 25-29
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
48
Issue
1
Year of publication
1998
Pages
25 - 29
Database
ISI
SICI code
0385-5414(1998)48:1<25:SFO1DV>2.0.ZU;2-2
Abstract
Irradiation of (Z)-N-substituted benzoyl-alpha-dehydrophenylalanines i n methanol with Pyrex-filtered light was found to selectively give 1-a zetine derivatives, which may be derived from 1,3-acyl migration of th e excited-state (E)-isomer, whereas no 1,5-acyl shift of the (Z)-isome r occurred owing to the stereoelectronic effects of the bulky aromatic acyl substituent.