An alkoxide-directed carbometalation of internal alkynes

被引：51

作者：

Ryan, J ^{[1
]}

Micalizio, GC ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 09期

关键词：

D O I：

10.1021/ja057352w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and efficient alkoxide-directed carbometalation is described. Regioselective carbon-carbon bond formation occurs in all cases at the site distal to the tethered alkoxide. This reaction provides a convenient means to prepare differentially functionalized tetrasubstituted 1,3-dienes in a regio- and stereoselective manner. Copyright © 2006 American Chemical Society.

引用

页码：2764 / 2765

页数：2

共 27 条

[1]

BAHADOOR A, 2006, IN PRESS ORG LETT, P8

[2] TRANSITION-METAL PROMOTED ALKYLATIONS OF ALKYNOLS [J].

COLEMAN, RA ;

ODOHERTY, CM ;

TWEEDY, HE ;

HARRIS, TV ;

THOMPSON, DW .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 107 (01) :C15-C17

[3] Phosphine-directed stereo- & regioselective Ni-catalyzed reactions of Grignard reagents with allylic ethers [J].

Didiuk, MT ;

Morken, JP ;

Hoveyda, AH .

TETRAHEDRON, 1998, 54 (07) :1117-1130

[4] INTRAMOLECULAR COORDINATIVE ASSISTANCE IN ADDITION OF GRIGNARD REAGENTS TO UNCONJUGATED CARBON-CARBON UNSATURATION [J].

EISCH, JJ ;

MERKLEY, JH .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 20 (01) :P27-&

[5] Titanium-mediated alkylative coupling of N-acylpyrroles [J].

Epstein, OL ;

Seo, JM ;

Masalov, N ;

Cha, JK .

ORGANIC LETTERS, 2005, 7 (11) :2105-2108

[6] Iron-catalyzed cross-coupling reactions:: Efficient synthesis of 2,3-allenol derivatives [J].

Fürstner, A ;

Méndez, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) :5355-5357

[7] Titanium alkoxide-based method for stereoselective synthesis of functionalized conjugated dienes [J].

Hamada, T ;

Suzuki, D ;

Urabe, H ;

Sato, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7342-7344

[8] GENERATION AND REACTIONS OF LOW-VALENT TITANIUM ALKOXIDE-ACETYLENE COMPLEXES - A PRACTICAL PREPARATION OF ALLYL ALCOHOLS [J].

HARADA, K ;

URABE, H ;

SATO, F .

TETRAHEDRON LETTERS, 1995, 36 (18) :3203-3206

[9] SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS [J].

HOVEYDA, AH ;

EVANS, DA ;

FU, GC .

CHEMICAL REVIEWS, 1993, 93 (04) :1307-1370

[10] STEREOSELECTIVE FORMATION OF CARBON CARBON BONDS THROUGH METAL CATALYSIS - THE ZIRCONIUM-CATALYZED ETHYLMAGNESATION REACTION [J].

HOVEYDA, AH ;

XU, ZM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5079-5080

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