Design of chiral N-triflyl phosphoramide as a strong chiral Bronsted acid and its application to asymmetric Diels-Alder reaction

被引：421

作者：

Nakashima, Daisuke ^{[1
]}

Yamamoto, Hisashi ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 30期

关键词：

D O I：

10.1021/ja062508t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly reactive and acidic chiral Brønsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels-Alder reaction of α,β-unsaturated ketone with silyloxydiene was demonstrated using this chiral Brønsted acid catalyst. Copyright © 2006 American Chemical Society.

引用

页码：9626 / 9627

页数：2

共 47 条

[1] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity
Akiyama, T
Tamura, Y
Itoh, J
Morita, H
Fuchibe, K
[J]. SYNLETT, 2006, (01) : 141 - 143
[2] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL
Akiyama, T
Saitoh, Y
Morita, H
Fuchibe, K
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1523 - 1526
[3] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
Akiyama, T
Morita, H
Itoh, J
Fuchibe, K
[J]. ORGANIC LETTERS, 2005, 7 (13) : 2583 - 2585
[4] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
Akiyama, T
Itoh, J
Yokota, K
Fuchibe, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
[5] Tris(trimethylsilyl)silyl-governed aldehyde cross-aldol cascade reaction
Boxer, MB
Yamamoto, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 48 - 49
[6] Burk P, 1996, J COMPUT CHEM, V17, P30, DOI 10.1002/(SICI)1096-987X(19960115)17:1<30::AID-JCC3>3.0.CO
[7] 2-1
[8] Synthesis and biological activity of N-sulfonylphosphoramidates:: Probing the electrostatic preferences of alkaline phosphatase
Burlingham, BT
Widlanski, TS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) : 7561 - 7567
[9] Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions
Futatsugi, K
Yamamoto, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1484 - 1487
[10] Trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide as a super Lewis acid catalyst for the condensation of trimethylhydroquinone with isophytol
Hasegawa, A
Ishihara, K
Yamamoto, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) : 5731 - 5733

← 1 2 3 4 5 →