Enantioselective ene reaction of cyclopentadiene and α,β-enals catalyzed by a diphenylprolinol silyl ether

被引：91

作者：

Gotoh, Hiroaki ^{[1
]}

Masui, Ryouhei ^{[1
]}

Ogino, Hiroshi ^{[1
]}

Shoji, Mitsuru ^{[1
]}

Hayashi, Yujiro ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 41期

关键词：

asymmetric synthesis; cyclopentadiene; Diels-Alder reaction; ene reaction; organocatalysis;

D O I：

10.1002/anie.200602925

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The opposite result: A diphenylprolinol silyl ether promotes an intermolecular enantioselective ene reaction of α,β-enals with cyclopentadiene. This is the first example of cyclopentadiene acting as the ene component, and not the diene, with α,β-enals. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6853 / 6856

页数：4

共 49 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
Ahrendt, KA
Borths, CJ
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
[2] Berkssel A., 2005, ASYMMETRIC ORGANOCAT
[3] CATALYTIC ASYMMETRIC CARBONYL-ENE REACTIONS
BERRISFORD, DJ
BOLM, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16): : 1717 - 1719
[4] BERRISFORD DJ, 1995, ANGEW CHEM, V107, P1862
[5] Brandau S., 2006, ANGEW CHEM, V118, P4411
[6] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
Brandau, Sven
Landa, Aitor
Franzen, Johan
Marigo, Mauro
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
[7] Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones
Chi, YG
Gellman, SH
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4253 - 4256
[8] Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids
Chi, Yonggui
Gellman, Samuel H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6804 - 6805
[9] Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[10] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175

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