ASYMMETRIC CYCLIZATION REACTIONS - CYCLIZATION OF SUBSTITUTED 4-PENTENALS INTO CYCLOPENTANONE DERIVATIVES BY RHODIUM(I) WITH CHIRAL LIGANDS

被引：71

作者：

TAURA, Y ^{[1
]}

TANAKA, M ^{[1
]}

WU, XM ^{[1
]}

FUNAKOSHI, K ^{[1
]}

SAKAI, K ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,MAIDASHI 3-1-1,HIGASHI KU,FUKUOKA 812,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 27期

关键词：

ASYMMETRIC CYCLIZATION; WILKINSON COMPLEX; RHODIUM; CHIRAL LIGAND; CYCLOPENTANONE;

D O I：

10.1016/S0040-4020(01)80954-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric cyclization of substituted 4-pentenals (Ia,b,c; IIa,b,c,d) by Rh(I) with chiral ligands was tested, and substrate (IId) with a bulkier substituent at C4 underwent more stereoselective cyclization by Rh(I)-((+)-DIPMC) to yield substituted cyclopentanone (IIId). The Rh(I) with (+)-DIPMC was found to proceed in a different manner from the Wilkinson-catalyzed cyclization.

引用

页码：4879 / 4888

页数：10

共 22 条

[1] ASYMMETRIC HYDROGENATION WITH NEW CHIRAL FUNCTIONALIZED BISPHOSPHINE-RHODIUM COMPLEXES [J].

ACHIWA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (25) :8265-8266

[2] TERPENE-FORMALDEHYDE REACTIONS .2. D-LIMONENE [J].

BLOMQUIS.AT ;

HIMICS, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (03) :1156-&

[3] A MECHANISTIC STUDY OF THE RHODIUM-CATALYZED CYCLIZATION OF 4-HEXENALS - REACTIONS OF DEUTERIO-4-HEXENALS [J].

CAMPBELL, RE ;

LOCHOW, CF ;

VORA, KP ;

MILLER, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5824-5830

[4] ENANTIOSELECTIVE CONJUGATE ADDITION OF RATIONALLY DESIGNED CHIRAL CUPRATE REAGENTS TO 2-CYCLOALKENONES [J].

COREY, EJ ;

NAEF, R ;

HANNON, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7114-7116

[5] HOMOGENEOUS CATALYSIS - MECHANISM OF CATALYTIC HYDROACYLATION - THE CONVERSION OF 4-PENTENALS TO CYCLOPENTANONES [J].

FAIRLIE, DP ;

BOSNICH, B .

ORGANOMETALLICS, 1988, 7 (04) :946-954

[6] HOMOGENEOUS CATALYSIS - CONVERSION OF 4-PENTENALS TO CYCLOPENTANONES BY EFFICIENT RHODIUM-CATALYZED HYDROACYLATION [J].

FAIRLIE, DP ;

BOSNICH, B .

ORGANOMETALLICS, 1988, 7 (04) :936-945

[7] STRUCTURAL REQUIREMENTS IN CHIRAL DIPHOSPHINE-RHODIUM COMPLEXES .11. ASYMMETRIC HOMOGENEOUS HYDROGENATION OF Z-ALPHA-ACYLAMINOCINNAMIC ACIDS AND ESTERS WITH (1S, 2S)-TRANS-1,2-BIS(DIPHENYLPHOSPHINOMETHYL) CYCLOHEXANE-RHODIUM(I) COMPLEXES [J].

GLASER, R ;

GERESH, S ;

BLUMENFELD, J ;

TWAIK, M .

TETRAHEDRON, 1978, 34 (15) :2405-2408

[8] STRUCTURAL REQUIREMENTS IN CHIRAL DIPHOSPHINE-RHODIUM COMPLEXES .12. ASYMMETRIC HOMOGENEOUS HYDROGENATION OF Z-ALPHA-N-METHYLACETAMIDOCINNAMIC ACID AND METHYL-ESTER CATALYZED BY RHODIUM(I) COMPLEXES OF DIOP AND ITS CARBOCYCLIC ANALOGS [J].

GLASER, R ;

GERESH, S ;

TWAIK, M ;

BENOITON, NL .

TETRAHEDRON, 1978, 34 (24) :3617-3621

[9]

HARRINGTON PJ, 1990, TRANSITION METALS TO

[10] SYNTHETIC STUDIES ON PROSTANOIDS .15. SYNTHESIS OF 11-METHYLPROSTAGLANDINS AND 11,11-DIMETHYLPROSTAGLANDINS VIA WITTIG REACTION OF ALPHA-DIENOL [J].

INOUE, K ;

SAKAI, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (08) :2361-2365

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