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

TitleIONIC CHIRAL HANDLE-INDUCED ASYMMETRIC-SYNTHESIS IN A SOLID-STATE NORRISH TYPE-II PHOTOREACTION
Publication TypeJournal Article
Year of Publication1994
AuthorsKoshima, H, Maeda, A, Masuda, N, Matsuura, T, Hirotsu, K, Okada, K, Mizutari, H, Ito, Y, Fu, TY, Scheffer, JR, Trotter, J
JournalTetrahedron-Asymmetry
Volume5
Pagination1415-1418
Date PublishedAug
Type of ArticleArticle
ISBN Number0957-4166
Keywords2, 4, 6-TRIISOPROPYLBENZOPHENONES, INDUCTION, PHOTOCHEMISTRY, SALTS
Abstract

Irradiation of crystals of salts formed between 4-(2,4,6-triisopropylbenzoyl)benzoic acid (1a) and various optically active amines is shown to lead to optically active Norrish type II photoproducts in low to moderate enantiomeric excesses, a process in which the ammonium ion has acted as an ’’ionic chiral handle.’’ X-ray crystallography reveals that the salts crystallize with two independent, mirror image-related molecules of the benzophenone moiety in the asymmetric unit, and this is suggested to be the source of the low ees observed.

URL<Go to ISI>://A1994PC67800004