Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions

被引：54

作者：

He, Hao ^{[1
]}

Pei, Bao-Jian ^{[1
]}

Chou, Ho-Hsuan ^{[1
]}

Tian, Tian ^{[1
]}

Chan, Wing-Hong ^{[1
]}

Lee, Albert W. M. ^{[1
]}

机构：

[1] Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 12期

关键词：

D O I：

10.1021/ol8005826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts; for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 degrees C to room temperature.

引用

页码：2421 / 2424

页数：4

共 50 条

[11] Diels-Alder reactions
Macquarrie, D
Dyson, P
GREEN CHEMISTRY, 2000, 2 (05) : G90 - G90
[12] Enantioselective Diels-Alder reactions of 3-(acyloxy)acrylates
Sibi, MP
Matsunaga, H
TETRAHEDRON LETTERS, 2004, 45 (30) : 5925 - 5929
[13] N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions
Corminboeuf, O
Renaud, P
ORGANIC LETTERS, 2002, 4 (10) : 1735 - 1738
[14] Enantioselective Diels-Alder reactions of 3-(acyloxy)acrylates
Matsunaga, H
Sibi, MP
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U361 - U361
[15] Catalytic enantioselective aza Diels-Alder reactions of imino dienophiles
Yao, SL
Johannsen, M
Hazell, RG
Jorgensen, KA
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (22) : 3121 - 3124
[16] DIELS-ALDER REACTIONS
BALDWIN, JE
CHEMISTRY & INDUSTRY, 1966, (08) : 333 - &
[17] DIELS-ALDER REACTIONS
FELL, B
ERDOL UND KOHLE ERDGAS PETROCHEMIE, 1966, 19 (04): : 304 - &
[18] Enantioselective Diels-Alder reactions catalyzed by samarium iodo binaphthoxides
Giuseppone, N
Santos, I
Collin, J
TETRAHEDRON LETTERS, 2000, 41 (05) : 639 - 642
[19] A novel hydrazide type organocatalyst for enantioselective Diels-Alder reactions
Suzuki, Ichiro
Ando, Masafumi
Shimabara, Rumiko
Hirata, Ai
Takeda, Kei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (08) : 3033 - 3040
[20] Enantioselective Organocatalytic Intramolecular Diels-Alder Reactions: A Computational Study
Duarte, Filipe J. S.
Gil Santos, A.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) : 3252 - 3261

← 1 2 3 4 5 →