Organic letters

Coupling of AlkynylTMS Derivatives with Vinylic Iodides. An Efficient Route to 1, 3-Enynes and Dienes

JA Marshall, HR Chobanian, MM Yanik

Index: Marshall, James A.; Chobanian, Harry R.; Yanik, Mathew M. Organic Letters, 2001 , vol. 3, # 25 p. 4107 - 4110

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Citation Number: 61

Abstract

We recently developed an efficient procedure for the resolution of 4-TMS-3-butyn-2-ol and found that the mesylate derivative (eg, 1) can be used for the in situ preparation of allenylindium reagents that undergo facile additions to branched and unbranched achiral and chiral aldehydes to afford adducts 2 in high yield with excellent diastereo- and enantiomeric selectivity (eq 1). 1 Pursuant to our interest in developing seamless integration of this methodology with reactions that ...

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