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Letter

Oxymercuration of Homoallylic Alcohol Derived Hemiacetals: Diastereoselective Synthesis of Protected 1,3-Diols

Supporting Info

Stella T. Sarraf and James L. Leighton*

Department of Chemistry, Columbia University, New York, New York 10027

Org. Lett., 2000, 2 (3), pp 403–405

DOI: 10.1021/ol991370z

Publication Date (Web): January 11, 2000

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

leighton@chem.columbia.edu

Abstract

Protected 1,3-diol synthons may be synthesized efficiently from homoallyic alcohols and simple aldehydes by oxymercuration of the derived hemiacetals. The reactions are diastereoselective and proceed without the use of solvent. Both Hg(OAc)₂ and HgClOAc are effective in the reaction, and the latter produces isolable organomercurial chlorides directly.

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