Tetrahedron letters

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 …

E Negishi, M Ay, YV Gulevich, Y Noda

Index: Negishi, Ei-ichi; Ay, Mehmet; Gulevich, Yuri V.; Noda, Yumiki Tetrahedron Letters, 1993 , vol. 34, # 9 p. 1437 - 1440

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Citation Number: 63

Abstract

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, eg, Pd (PPh 3) 4 or Cl 2 Pd (PPh 3) 2 and n-BuLi (2 equiv), in DMF provides a highly stereoselective (>-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 ...