A catalytic carbon-phosphorus ylide reaction: Phosphane-catalyzed annulation of allylic compounds with electron-deficient alkenes

被引：223

作者：

Du, YH ^{[1
]}

Lu, XY ^{[1
]}

Zhang, CM ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 09期

关键词：

D O I：

10.1002/anie.200390266

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Readily available starting materials and high selectivity: These are two appealing features of the phosphane-catalyzed carbon-phosphorus ylide reaction described. Bromide, acetate, of tert-butyl carbonate derivatives of adducts formed by the Morita-Baylis-Hillman reaction react with PPh3 to form an allylic ylide. Phosphane-catalyzed annulation of the ylides with electron-deficient alkenes results in the facile construction of cyclopentenes [Eq. (1)]. X = Br, OAc, OBoc; E = CO2Et.

引用

页码：1035 / +

页数：4

共 41 条

[1]

Aggarwal V. K., 2001, ANGEW CHEM, V113, P1482

[2]

Aggarwal VK, 1998, SYNLETT, P329

[3]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO

[4]

2-W

[5]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[6]

2-E

[7] NEW SYNTHESIS OF CYCLOHEXADIENE DERIVATIVES [J].

BOHLMANN, F ;

ZDERO, C .

CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (12) :3779-3787

[8] SYNTHETIC STUDIES ON DAMASCENONES [J].

BUCHI, G ;

WUEST, H .

HELVETICA CHIMICA ACTA, 1971, 54 (07) :1767-&

[9]

DAUBEN WG, 1973, TETRAHEDRON LETT, P4425

[10]

DAUBEN WG, 1973, TETRAHEDRON LETT, P3711

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