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

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
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DOI:
10.1016/s0040-4039(00)60312-x
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发表时间:
1993-02-26
影响因子:
1.8
通讯作者:
NODA, Y
NODA, Y
中科院分区:
化学4区
文献类型:
--
作者:
NEGISHI, E;AY, M;NODA, Y

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Zn-保护的(Z)-3-碘-2-丁烯-1-醇与有机锌在1- 5mol%的Pd络合物,例如,Pd(PPh 3)4或Cl 2 Pd(PPh 3)2和n-BuLi(2当量)在DMF中的混合物提供了制备(Z)-3-甲基-2-阿尔肯-1-醇的高度立体选择性(大于或等于96%)、通用和高产率的方法,而单独使用含B和Sn的有机金属沿着Pd催化剂或有机铜以中等至良好的产率得到所需产物。
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.