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


Negishi E., AY M. , GULEVICH Y., Noda Y.

TETRAHEDRON LETTERS, vol.34, no.9, pp.1437-1440, 1993 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 9
  • Publication Date: 1993
  • Doi Number: 10.1016/s0040-4039(00)60312-x
  • Title of Journal : TETRAHEDRON LETTERS
  • Page Numbers: pp.1437-1440

Abstract

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.