IONIC CHIRAL HANDLE-INDUCED ASYMMETRIC-SYNTHESIS IN A SOLID-STATE NORRISH TYPE-II PHOTOREACTION

Authors
KOSHIMA H MAEDA A MASUDA N MATSUURA T HIROTSU K OKADA K MIZUTARI H ITO Y FU TY SCHEFFER JR TROTTER J
Citation
H. Koshima et al., IONIC CHIRAL HANDLE-INDUCED ASYMMETRIC-SYNTHESIS IN A SOLID-STATE NORRISH TYPE-II PHOTOREACTION, Tetrahedron : asymmetry, 5(8), 1994, pp. 1415-1418
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
8
Year of publication
1994
Pages
1415 - 1418
Database
ISI
SICI code
0957-4166(1994)5:8<1415:ICHAIA>2.0.ZU;2-F
Abstract
Irradiation of crystals of salts formed between 4-(2,4,6-triisopropylb enzoyl)benzoic acid (1a) and various optically active amines is shown to lead to optically active Norrish type II photoproducts in low to mo derate enantiomeric excesses, a process in which the ammonium ion has acted as an ''ionic chiral handle.'' X-ray crystallography reveals tha t the salts crystallize with two independent, mirror image-related mol ecules of the benzophenone moiety in the asymmetric unit, and this is suggested to be the source of the low ees observed.