HIGHLY STEREOSELECTIVE AND GENERAL-SYNTHESIS OF (Z)-3-METHYL-2-ALKEN-1-OLS VIA PALLADIUM-CATALYZED CROSS COUPLING OF (Z)-3-IODO-2-BUTEN-1-OL WITH ORGANOZINCS AND OTHER ORGANOMETALS

被引：56

作者：

NEGISHI, E

AY, M

GULEVICH, YV

NODA, Y

机构：

[1] Department of Chemistry, Purdue University, West Lafayette

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)60312-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of Zn-protected (Z)-3-iodo-2-buten-1-ol with organozincs in the presence of 1-5 mol % of a Pd complex, e.g., Pd(PPh3)4 or Cl2Pd(pPh3)2 and n-BuLi (2 equiv), in DMF provides a highly stereoselective (greater-than-or-equal-to 96%), general, and high-yielding procedure for preparing (Z)-3-methyl-2-alken-1-ols, while the use of organometals containing B and Sn along with a Pd catalyst or organocoppers alone gives the desired products in moderate to good yields.

引用

页码：1437 / 1440

页数：4

共 33 条

[1] THE CROSS-COUPLING REACTIONS OF ORGANIC HALIDES WITH ORGANIC DERIVATIVES OF TIN, MERCURY AND COPPER CATALYZED BY PALLADIUM [J].