Asymmetric induction in organic photochemistry via the solid-state ionic chiral auxiliary approach

被引:60
作者
Scheffer, JR [1 ]
Xia, WJ [1 ]
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
来源
ORGANIC SOLID STATE REACTIONS | 2005年 / 254卷
关键词
asymmetric induction; organic photochemistry; solid state; ionic chiral auxiliaries; crystal structure-reactivity correlations;
D O I
10.1007/b101000
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
After a brief introduction and summary of various methods of asymmetric induction in organic photochemistry, the main part of the review covers the solid-state ionic chiral auxiliary approach to asymmetric photochemical synthesis. Application of this technique to the Norrish type II reaction, as well as to the di-Ti-methane and oxa-di-pi-methane photorearrangements, and the Cis, trans-photoisomerization of diarylcyclopropane derivatives is presented and discussed.
引用
收藏
页码:233 / 262
页数:30
相关论文
共 58 条
[1]  
[Anonymous], 1991, PHOTOCHEMISTRY ORG C
[2]  
[Anonymous], ADV PHOTOCHEM
[3]  
Breck D. W., 1973, Zeolite Molecular Sieves: Structure, Chemistry, and Use
[4]  
BUSCHMANN H, 1991, ANGEW CHEM INT EDIT, V30, P47
[5]   OPTICAL-ACTIVITY CAN BE CREATED FROM NOTHING [J].
CASWELL, L ;
GARCIAGARIBAY, MA ;
SCHEFFER, JR ;
TROTTER, J .
JOURNAL OF CHEMICAL EDUCATION, 1993, 70 (10) :785-787
[6]   PHOTOCYCLIZATION OF ALPHA-KETO AMIDES IN HOMOGENEOUS SOLUTION AND AQUEOUS CYCLODEXTRIN MEDIA - THE ROLE OF ZWITTERIONS AND DIRADICALS IN PHOTOINDUCED ELECTRON-TRANSFER REACTIONS [J].
CHESTA, CA ;
WHITTEN, DG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2188-2197
[7]   Linearly conjugated benzocyclohexadienone photochemistry in the solid state: ionic chiral auxiliary mediated asymmetric induction [J].
Cheung, E ;
Netherton, MR ;
Scheffer, JR ;
Trotter, J .
TETRAHEDRON LETTERS, 1999, 40 (50) :8737-8740
[8]   An investigation of the solid-state photochemistry of α-mesitylacetophenone derivatives:: Asymmetric induction studies and crystal structure-reactivity relationships [J].
Cheung, E ;
Rademacher, K ;
Scheffer, JR ;
Trotter, J .
TETRAHEDRON, 2000, 56 (36) :6739-6751
[9]   In the footsteps of Pasteur: Asymmetric induction in the solid-state photochemistry of ammonium carboxylate salts [J].
Cheung, E ;
Netherton, MR ;
Scheffer, JR ;
Trotter, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) :2919-2920
[10]   Conformational enantiomerism in chiral organic salts containing crystallographically independent anion-cation pairs [J].
Cheung, E ;
Kang, T ;
Netherton, MR ;
Scheffer, JR ;
Trotter, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (47) :11753-11754