共 36 条
Catalytic enantioselective synthesis of flavanones and chromanones
被引:277
作者:

Biddle, Margaret M.
论文数: 0 引用数: 0
h-index: 0
机构:
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

Lin, Michael
论文数: 0 引用数: 0
h-index: 0
机构:
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

Scheidt, Karl A.
论文数: 0 引用数: 0
h-index: 0
机构:
Northwestern Univ, Dept Chem, Evanston, IL 60208 USA Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
机构:
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词:
D O I:
10.1021/ja070394v
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a beta-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the beta-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.
引用
收藏
页码:3830 / +
页数:3
相关论文
共 36 条
- [31] Asymmetric organocatalysis with novel chiral thiourea derivatives: Bifunctional catalysts for the Strecker and nitro-Michael reactions[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (23) : 4995 - 5000Tsogoeva, SB论文数: 0 引用数: 0 h-index: 0机构: Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, GermanyYalalov, DA论文数: 0 引用数: 0 h-index: 0机构: Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, GermanyHateley, MJ论文数: 0 引用数: 0 h-index: 0机构: Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, GermanyWeckbecker, C论文数: 0 引用数: 0 h-index: 0机构: Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, GermanyHuthmacher, K论文数: 0 引用数: 0 h-index: 0机构: Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
- [32] Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts[J]. ORGANIC LETTERS, 2005, 7 (10) : 1967 - 1969Vakulya, B论文数: 0 引用数: 0 h-index: 0机构: Hungarian Acad Sci, Chem Res Ctr, Inst Biomol Chem, H-1525 Budapest, HungaryVarga, S论文数: 0 引用数: 0 h-index: 0机构: Hungarian Acad Sci, Chem Res Ctr, Inst Biomol Chem, H-1525 Budapest, HungaryCsámpai, A论文数: 0 引用数: 0 h-index: 0机构: Hungarian Acad Sci, Chem Res Ctr, Inst Biomol Chem, H-1525 Budapest, HungarySoós, T论文数: 0 引用数: 0 h-index: 0机构: Hungarian Acad Sci, Chem Res Ctr, Inst Biomol Chem, H-1525 Budapest, Hungary
- [33] Organocatalytic enantioselective conjugate additions to enones[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12652 - 12653Wang, Jian论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R ChinaLi, Hao论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R ChinaZu, Liansuo论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R ChinaJiang, Wei论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R ChinaXie, Hexin论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R ChinaDuan, Wenhu论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R ChinaWang, Wei论文数: 0 引用数: 0 h-index: 0机构: E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
- [34] Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives[J]. CHEMICAL COMMUNICATIONS, 2005, (35) : 4481 - 4483Ye, JX论文数: 0 引用数: 0 h-index: 0机构: Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, EnglandDixon, DJ论文数: 0 引用数: 0 h-index: 0机构: Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, EnglandHynes, PS论文数: 0 引用数: 0 h-index: 0机构: Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
- [35] Highly enantioselective thiourea-catalyzed nitro-Mannich reactions[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) : 466 - 468Yoon, TP论文数: 0 引用数: 0 h-index: 0机构: Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USAJacobsen, EN论文数: 0 引用数: 0 h-index: 0机构: Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
- [36] Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether[J]. TETRAHEDRON LETTERS, 2006, 47 (29) : 5131 - 5134Zu, Liansuo论文数: 0 引用数: 0 h-index: 0机构: Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USALi, Hao论文数: 0 引用数: 0 h-index: 0机构: Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USAWang, Jian论文数: 0 引用数: 0 h-index: 0机构: Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USAYu, Xinhong论文数: 0 引用数: 0 h-index: 0机构: Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USAWang, Wei论文数: 0 引用数: 0 h-index: 0机构: Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA