Vital role of entropy in photochirogenesis

被引:33
作者
Inoue, Y [1 ]
Sugahara, N [1 ]
Wada, T [1 ]
机构
[1] JST, Inoue Photochirogenesis Project, ERATO, Toyonaka, Osaka 5650085, Japan
关键词
D O I
10.1351/pac200173030475
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The effects of temperature, pressure, solvent, and substrate concentration upon several enantio- and diastereodifferentiating photochemical reactions have been investigated and discussed in detail. These entropy-related external factors, which manipulate the weak electronic and steric interactions in the excited state, dynamically control the stereochemical outcome of asymmetric photochemical reactions, and even switch the product chirality. A global view on the "entropy chemistry" and its potential applications are also discussed.
引用
收藏
页码:475 / 480
页数:6
相关论文
共 28 条
[1]  
[Anonymous], ADV PHOTOCHEM
[2]   ACTIVATION AND REACTION VOLUMES IN SOLUTION [J].
ASANO, T ;
LENOBLE, J .
CHEMICAL REVIEWS, 1978, 78 (04) :407-489
[3]   Enantiodifferentiating anti-Markovnikov photoaddition of alcohols to 1,1-diphenylalkenes sensitized by chiral naphthalenecarboxylates [J].
Asaoka, S ;
Kitazawa, T ;
Wada, T ;
Inoue, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (37) :8486-8498
[4]  
Asaoka S., 2000, J CHEM SOC P2, P737
[5]   HIGH-PRESSURE STUDY OF THE EFFECT OF VISCOSITY ON FLUORESCENCE AND PHOTOISOMERIZATION OF TRANS-STILBENE [J].
BREY, LA ;
SCHUSTER, GB ;
DRICKAMER, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :129-134
[6]   PRESSURE-INDUCED DIASTEREOSELECTIVITY IN PHOTOCHEMICAL [2 + 2] CYCLOADDITION REACTIONS [J].
BUBACK, M ;
BUNGER, J ;
TIETZE, LF .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (11) :2577-2582
[7]   RADICAL IONS AND PHOTOCHEMICAL CHARGE-TRANSFER PHENOMENA .22. PRESSURE-INDUCED DIASTEREOSELECTIVITY IN PHOTOINDUCED DIELS-ALDER REACTIONS [J].
CHUNG, WS ;
TURRO, NJ ;
MERTES, J ;
MATTAY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4881-4887
[8]  
Everitt SRL, 1999, MOL SUPRAM PHOTOCHEM, V3, P71
[9]   Enantioselectivity of lipase catalyzed transesterification between tributyrylglycerol and 2-octanol in organic solvents [J].
Hirata, H ;
Miyagishi, M ;
Mayama, M .
NIPPON KAGAKU KAISHI, 1998, (02) :113-118
[10]   Trapped optically active (E)-cycloheptene generated by enantiodifferentiating Z-E photoisomerization of cycloheptene sensitized by chiral aromatic esters [J].
Hoffmann, R ;
Inoue, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (46) :10702-10710