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

被引：27

作者：

KOSHIMA, H

MAEDA, A

MASUDA, N

MATSUURA, T

HIROTSU, K

OKADA, K

MIZUTARI, H

ITO, Y

FU, TY

SCHEFFER, JR

TROTTER, J

机构：

[1] RYUKOKU UNIV,DEPT CHEM MAT,OTSU 520,JAPAN

[2] OSAKA CITY UNIV,DEPT CHEM,SUMIYOSHI KU,OSAKA 558,JAPAN

[3] KYOTO UNIV,DEPT SYNTHET CHEM,KYOTO,KYOTO 606,JAPAN

[4] UNIV BRITISH COLUMBIA,DEPT CHEM,VANCOUVER V6T 1Z1,BC,CANADA

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 08期

关键词：

D O I：

10.1016/0957-4166(94)80099-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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.

引用

页码：1415 / 1418

页数：4

共 9 条

[1] ASYMMETRIC INDUCTION IN THE SOLID-STATE PHOTOCHEMISTRY OF SALTS OF CARBOXYLIC-ACIDS WITH OPTICALLY-ACTIVE AMINES
GUDMUNDSDOTTIR, AD
SCHEFFER, JR
[J]. TETRAHEDRON LETTERS, 1990, 31 (47) : 6807 - 6810
[2] IONIC CHIRAL HANDLE-INDUCED SOLID-STATE ASYMMETRIC-SYNTHESIS - ORIGIN OF THE ASYMMETRIC INDUCTION ELUCIDATED THROUGH ABSOLUTE-CONFIGURATION CORRELATION STUDIES
GUDMUNDSDOTTIR, AD
SCHEFFER, JR
TROTTER, J
[J]. TETRAHEDRON LETTERS, 1994, 35 (09) : 1397 - 1400
[3] ASYMMETRIC INDUCTION IN THE SOLID-STATE PHOTOCHEMISTRY OF AMMONIUM-SALTS
GUDMUNDSDOTTIR, AD
SCHEFFER, JR
[J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1991, 54 (04) : 535 - 538
[4] PHOTOINDUCED REACTIONS .142. INTRAMOLECULAR HYDROGEN ABSTRACTION FROM TRIPLET-STATES OF 2,4,6-TRIISOPROPYLBENZOPHENONES - IMPORTANCE OF HINDERED ROTATION IN EXCITED-STATES
ITO, Y
NISHIMURA, H
UMEHARA, Y
YAMADA, Y
TONE, M
MATSUURA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) : 1590 - 1597
[5] EFFICIENCY FOR SOLID-STATE PHOTOCYCLIZATION OF 2,4,6-TRIISOPROPYLBENZOPHENONES
ITO, Y
MATSUURA, T
FUKUYAMA, K
[J]. TETRAHEDRON LETTERS, 1988, 29 (25) : 3087 - 3090
[6] BIMOLECULAR SOLID-STATE PHOTOREACTIONS
ITO, Y
[J]. MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1992, 219 : 29 - 36
[7] CRYSTAL TO MOLECULAR CHIRALITY TRANSFER - SUPRAMOLECULAR PHOTOCHEMISTRY OF CRYSTALLINE CARBOXYLATE SALTS
JONES, R
SCHEFFER, JR
TROTTER, J
YANG, J
[J]. TETRAHEDRON LETTERS, 1992, 33 (38) : 5481 - 5484
[8] SCHEFFER JR, 1987, ORGANIC SOLID STATE, pCH1
[9] WAGNER PJ, 1991, ORGANIC PHYTOCHEMIST, V11, pCH1

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