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
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
收藏
页码:1636 / 1639
页数:4
相关论文
共 48 条
[1]   PHOTO-POLYMERIZATION IN CHIRAL CRYSTALS .4. ENGINEERING OF CHIRAL CRYSTALS FOR ASYMMETRIC (2-PI + 2-PI) PHOTO-POLYMERIZATION - EXECUTION OF AN ABSOLUTE ASYMMETRIC-SYNTHESIS WITH QUANTITATIVE ENANTIOMERIC YIELD [J].
ADDADI, L ;
VANMIL, J ;
LAHAV, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3422-3429
[2]  
Amirsakis DG, 2001, ANGEW CHEM INT EDIT, V40, P4256, DOI 10.1002/1521-3773(20011119)40:22<4256::AID-ANIE4256>3.0.CO
[3]  
2-S
[4]  
[Anonymous], 1991, PHOTOCHEMISTRY ORG C
[5]   SOLID-STATE PHOTOCHEMISTRY OF N,N-DIALKYL-ALPHA-OXOAMIDES - TYPE-II REACTIONS IN THE CRYSTALLINE STATE [J].
AOYAMA, H ;
HASEGAWA, T ;
OMOTE, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) :5343-5347
[6]   KALEIDOSCOPIC PHOTOREACTION BEHAVIOR OF ALKYL 4-[2-(4-PYRIDYL)ETHENYL]CINNAMATE CRYSTALS - A CRYSTALLINE LINEAR HIGH POLYMER FROM THE METHYL-ESTER, AN ABSOLUTE ASYMMETRIC REACTION OF THE ETHYL-ESTER, AND 2 TYPES OF DIMER FORMATION FROM THE PROPYL ESTER [J].
CHUNG, CM ;
HASEGAWA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7311-7316
[7]   Electrochemistry and electrogenerated chemiluminescence from silicon nanocrystal quantum dots [J].
Ding, ZF ;
Quinn, BM ;
Haram, SK ;
Pell, LE ;
Korgel, BA ;
Bard, AJ .
SCIENCE, 2002, 296 (5571) :1293-1297
[8]   USE OF CHIRAL SINGLE-CRYSTALS TO CONVERT ACHIRAL REACTANTS TO CHIRAL PRODUCTS IN HIGH OPTICAL YIELD - APPLICATION TO THE DI-PI-METHANE AND NORRISH TYPE-II PHOTOREARRANGEMENTS [J].
EVANS, SV ;
GARCIAGARIBAY, M ;
OMKARAM, N ;
SCHEFFER, JR ;
TROTTER, J ;
WIREKO, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5648-5650
[9]   The ionic auxiliary concept in solid state organic photochemistry [J].
Gamlin, JN ;
Jones, R ;
Leibovitch, M ;
Patrick, B ;
Scheffer, JR ;
Trotter, J .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (04) :203-209
[10]   X-ray analysis of structural changes in photochromic salicylideneaniline crystals. Solid-state reaction induced by two-photon excitation [J].
Harada, J ;
Uekusa, H ;
Ohashi, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5809-5810