Tetrahedron letters

C 5-Branched vinyltin acetals as versatile tools for terpenic synthesis

I Beaudet, V Launay, JL Parrain, JP Quintard

Index: Beaudet, Isabelle; Launay, Valerie; Parrain, Jean-Luc; Quintard, Jean-Paul Tetrahedron Letters, 1995 , vol. 36, # 3 p. 389 - 392

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Citation Number: 22

Abstract

Typical procedure for the preparation of 2: Bu 3 SnMgMe was obtained at −20°C by addition of MeMgI (78 mmol, 3.2 M in ether) to Bu 3 SnLi (78 mmol, in 40 ml THF) previously prepared by deprotonation of Bu 3 SnH with iPr 2 NLi. At −20°C, the Bu 3 SnMgMe solution was subsequently stirred with CuCN (5% mol) before dropwise addition of alkyne (0.4 eq) and quenching with methyl iodide (2.3 eq). After usual workup, vinyltin 2 was isolated by distillation (Eb 0.06 = 114°C).