A new type of catalytic tandem 1,4-addition-aldol reaction which proceeds through an (oxa-π-allyl)rhodium intermediate

被引：88

作者：

Yoshida, K ^{[1
]}

Ogasawara, M ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 37期

关键词：

D O I：

10.1021/ja0271025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 9-aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) with α,β-unsaturated ketones and aldehydes in the presence of 3 mol % [Rh(OMe)(cod)]2 in toluene at 20 °C for 2 h gave high yields of the tandem 1,4-addition-aldol reaction products with high syn selectivity. The reaction proceeds through the catalytic cycle consisting of 1,4-addition of an organorhodium species to an α,β-unsaturated ketone and the aldol addition of the resulting (oxa-π-allyl)rhodium intermediate to an aldehyde. Copyright © 2002 American Chemical Society.

引用

页码：10984 / 10985

页数：2

共 7 条

[1] Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions
Howell, Gareth P.
Fletcher, Stephen P.
Geurts, Koen
Ter Horst, Bjorn
Feringa, Ben L.
Journal of the American Chemical Society, 2006, 128 (46): : 14977 - 14985
[2] Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions
Howell, Gareth P.
Fletcher, Stephen P.
Geurts, Koen
ter Horst, Bjorn
Feringa, Ben L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14977 - 14985
[3] Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction
Arnold, LA
Naasz, R
Minnaard, AJ
Feringa, BL
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21): : 7244 - 7254
[4] Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal
Arnold, LA
Naasz, R
Minnaard, AJ
Feringa, BL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) : 5841 - 5842
[5] Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal [2]
Arnold, L.A.
Naasz, R.
Minnaard, A.J.
Feringa, B.L.
1600, American Chemical Society (123):
[6] Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates
Hayashi, T
Takahashi, M
Takaya, Y
Ogasawara, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) : 5052 - 5058
[7] New bidentate chiral phosphoramidites in copper-catalyzed asymmetric 1,4-addition of diethylzinc to cyclic α,β-enones:: enantioselective tandem 1,4-addition-aldol reactions with 2-cyclopentenone
Mandoli, A
Arnold, LA
de Vries, AHM
Salvadori, P
Feringa, BL
TETRAHEDRON-ASYMMETRY, 2001, 12 (13) : 1929 - 1937

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