VAPOL phosphoric acid catalysis: the highly enantioselective addition of imides to imines

被引:95
作者
Liang, Yuxue [1 ]
Rowland, Emily B. [1 ]
Rowland, Gerald B. [1 ]
Perman, Jason A. [1 ]
Antilla, Jon C. [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
关键词
D O I
10.1039/b709276h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first highly enantioselective catalytic method for the preparation of chiral aminals via the addition of imide nucleophiles to imines is reported.
引用
收藏
页码:4477 / 4479
页数:3
相关论文
共 25 条
[1]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[2]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347
[3]   A DOZEN YEARS OF RETRO-INVERSO PEPTIDOMIMETICS [J].
CHOREV, M ;
GOODMAN, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (05) :266-273
[4]   RECENT DEVELOPMENTS IN RETRO PEPTIDES AND PROTEINS - AN ONGOING TOPOCHEMICAL EXPLORATION [J].
CHOREV, M ;
GOODMAN, M .
TRENDS IN BIOTECHNOLOGY, 1995, 13 (10) :438-445
[5]   Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].
Connon, Stephen J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912
[6]   PROTECTED DIAMINOMETHANE [J].
DEBONS, FE ;
LOUDON, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1703-1704
[7]   Partially modified retro-inverso peptides: Development, synthesis, and conformational behavior [J].
Fletcher, MD ;
Campbell, MM .
CHEMICAL REVIEWS, 1998, 98 (02) :763-795
[8]   CONCEPT OF LINEAR MODIFIED RETRO-PEPTIDE STRUCTURES [J].
GOODMAN, M ;
CHOREV, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (01) :1-7
[9]  
GREENE EW, 1999, PROTECTIVE GROUPS OR
[10]   Ni-to-Ni+3-ethylene-bridged partially modified retro-inversotetrapeptide β-turn mimetic:: Design, synthesis, and structural characterization [J].
Han, YL ;
Giragossian, C ;
Mierke, DF ;
Chorev, M .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5085-5097