Unprecedented carbocyclization of 1,6-allenynes on addition of organoboronic acids under Pd-catalysis

被引：25

作者：

Gupta, AK ^{[1
]}

Rhim, CY ^{[1
]}

Oh, CH ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Sungdong Gu, Seoul 133791, South Korea

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 13期

关键词：

D O I：

10.1016/j.tetlet.2005.02.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to the ene behavior of allenes in Pauson-Khand reactions and other cyclization reactions, 1,6-allenynes undergo unprecedented carbocyclization followed by regioselective addition of organoboronic acids in the presence of Pd(OAc)(2) and tri-t-butyl phosphine under mild reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2247 / 2250

页数：4

共 28 条

[21]

Pagenkopf BL, 2000, SYNTHESIS-STUTTGART, P1009

[22]

SHENGMING M, 1999, J AM CHEM SOC, V121, P7943

[23] Chemo- and regioselective intramolecular hydrosilylative carbocyclization of allenynes [J].

Shibata, T ;

Kadowaki, S ;

Takagi, K .

ORGANOMETALLICS, 2004, 23 (17) :4116-4120

[24] Rhodium complex-catalyzed intramolecular ene-type reaction of allenynes [J].

Shibata, T ;

Takesue, Y ;

Kadowaki, S ;

Takagi, K .

SYNLETT, 2003, (02) :268-270

[25] Iridium complex-catalyzed Pauson-Khand-type reaction of allenynes [J].

Shibata, T ;

Kadowaki, S ;

Hirase, M ;

Takagi, K .

SYNLETT, 2003, (04) :573-575

[26] Regio- and stereochemical control in bis-functionalization-cyclization: Use of alleneyne precursors for carbocyclic and heterocyclic synthesis [J].

Shin, S ;

RajanBabu, TV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8416-8417

[27] Non-metathesis ruthenium-catalyzed C-C bond formation [J].

Trost, BM ;

Toste, FD ;

Pinkerton, AB .

CHEMICAL REVIEWS, 2001, 101 (07) :2067-2096

[28] Palladium-catalyzed reactions of allenes [J].

Zimmer, R ;

Dinesh, CU ;

Nandanan, E ;

Khan, FA .

CHEMICAL REVIEWS, 2000, 100 (08) :3067-3125

← 1 2 3 →