A novel direct catalytic asymmetric synthesis of cyclic indole derivatives by intramolecular carbopalladation of allenes and subsequent intramolecular amination

被引：35

作者：

Hiroi, K ^{[1
]}

Hiratsuka, Y ^{[1
]}

Watanabe, K ^{[1
]}

Abe, I ^{[1
]}

Kato, F ^{[1
]}

Hiroi, M ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(02)00359-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel asymmetric synthetic method allowing a facile entry to chiral cyclic indole compounds has been developed by means of asymmetric carbopalladation-amination of allenes using a palladium catalyst with chiral phosphine ligands: intramolecular carbopalladation of allenes, which bear o-iodophenyl amino groups, was followed by intramolecular amination of the resultant n-allylpalladium intermediates. The enantioselectivity of the asymmetric reactions were found to be dependant on the chiral phosphine ligands and the solvent used; N-methylpyridone was the most effective solvent for achieving efficient enantioselectivity with high chemical yields, and (S)-(-)-BINAP or (S)-Tol-BINAP were revealed to be the most useful of the chiral phosphine ligands examined, depending on the substrate employed. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1351 / 1353

页数：3

共 23 条

[1]

AHAMAR M, 1987, TETRAHEDRON, V43, P513

[2] SYNTHESIS OF 1,3-DIENES AND FUNCTIONALIZED STYRENES BY CATALYTIC CARBOPALLADATION OF ALLENES [J].

AHMAR, M ;

CAZES, B ;

GORE, J .

TETRAHEDRON LETTERS, 1984, 25 (40) :4505-4508

[3] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].

Ashimori, A ;

Bachand, B ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487

[4] CARBOPALLADATION OF FUNCTIONALIZED ALLENES - REGIOSELECTIVITY OF THE REACTION OF CARBONUCLEOPHILES WITH THE INTERMEDIATE PI-ALLYL PALLADIUM COMPLEXES [J].

CHAPTAL, N ;

COLOVRAYGOTTELAND, V ;

GRANDJEAN, C ;

CAZES, B ;

GORE, J .

TETRAHEDRON LETTERS, 1991, 32 (15) :1795-1798

[5] Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from α-Amino allenes [J].

Dieter, RK ;

Yu, H .

ORGANIC LETTERS, 2001, 3 (24) :3855-3858

[6] VINYL TRIFLUOROSULFONATES IN THE CARBOPALLADATION OF ALLENIC HYDROCARBONS [J].

FRIESS, B ;

CAZES, B ;

GORE, J .

TETRAHEDRON LETTERS, 1988, 29 (33) :4089-4092

[7]

GRIESBAUM K, 1966, ANGEW CHEM, V78, P953

[8]

Hiroi K, 2001, SYNLETT, P263

[9] Asymmetric direct α,β-functionalization of allenes via asymmetric carbopalladation [J].

Hiroi, K ;

Kato, F ;

Yamagata, A .

CHEMISTRY LETTERS, 1998, (05) :397-398

[10]

HIROI K, 1996, ANN REPORT TOHOKU CO, V43, P1

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