Absolute asymmetric photocyclization of a photochromic diarylethene derivative in single crystals

被引：100

作者：

Yamamoto, S ^{[1
]}

Matsuda, K ^{[1
]}

Irie, M ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Higashi Ku, Fukuoka 8128581, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 14期

关键词：

asymmetric synthesis; chirality; enantioselectivity; photochemistry; photochromism;

D O I：

10.1002/anie.200250417

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chirality from the crystal lattice: The achiral diarylethene 1 a crystallizes in a monoclinic chiral space group, that is, two different kinds of crystals, (M)-1 a and (P)-1 a, are obtained. Photoirradiation of (P)-1 a furnished optically pure closed-ring isomer (R,R)-1 b in the single crystal (see scheme). The photochemical cycles can be repeated by alternating UV and visible photoirradiation.

引用

页码：1636 / 1639

页数：4

共 48 条

[41] ENANTIOSELECTIVE PHOTOCONVERSION OF PYRIDONES INTO BETA-LACTAM DERIVATIVES IN INCLUSION COMPLEXES WITH OPTICALLY-ACTIVE HOST COMPOUNDS [J].

TODA, F ;

TANAKA, K .

TETRAHEDRON LETTERS, 1988, 29 (34) :4299-4302

[42] HIGHLY ENANTIOSELECTIVE PHOTOCYCLIZATION OF N-(ARYLOYLMETHYL)-DELTA-VALEROLACTAMS [J].

TODA, F ;

TANAKA, K ;

KAKINOKI, O ;

KAWAKAMI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3783-3784

[43]

Williams D.J., 2001, ANGEW CHEM, V113, P4386

[44] X-ray crystallographic study on single-crystalline photochromism of 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene [J].

Yamada, T ;

Kobatake, S ;

Irie, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (10) :2179-2184

[45] Single-crystalline photochromism of diarylethene mixtures [J].

Yamada, T ;

Kobatake, S ;

Irie, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (01) :167-173

[46] Crystal structure-reactivity correlation in single-crystalline photochromism of 1,2-bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene [J].

Yamada, T ;

Muto, K ;

Kobatake, S ;

Irie, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) :6164-6168

[47] X-ray crystallographic study on single-crystalline photochromism of bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene [J].

Yamada, T ;

Kobatake, S ;

Muto, K ;

Irie, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1589-1592

[48] Asymmetric photocyclization of diarylethene derivatives [J].

Yamaguchi, T ;

Uchida, K ;

Irie, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (26) :6066-6071

← 1 2 3 4 5 →