Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using alpha-alkoxypropargylstannanes

Academic Article
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publication date

  • 2001

abstract

  • Propargylic 1,2-anti-diol derivatives 2 and 10 are prepared in high yield and excellent diastereoselectivity by addition of alpha-alkoxypropargylstannanes 4a and 4b to aldehydes in the presence of BuSnCl(3). We also introduce the use of KF on Celite as a convenient and mild reagent for removal of the organotin waste products of these reactions. Reaction: see text.