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Synfacts 2006(11): 1138-1138  
DOI: 10.1055/s-2006-949444
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Z-Iodoallylic Iodides from Propargyl Alcohols

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
G. Manickam, U. Siddappa, Y. Li*
Syngene International Pvt. Ltd., Banganlore , India and Kosan Biosciences Inc., Hayward, USA
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

Due to the utility of iodides in synthetic chemistry, the authors sought a practical route to allylic vinyl diiodides. This challenge was accomplished and afforded Z-iodoallylic iodides with high selectivity and high yield. Only a catalytic amount of ZnCl2 was needed (10-15 mol%), as well as 2.2 equiv of TMSI as the iodide source. Importantly, homopropargyl alcohols work also well, although the Z-selectivity is somewhat diminished.