Synthesis of 1,5-Enynes by Brønsted Acid Catalyzed Substitution of Propargylic Alcohols and One-Pot Synthesis of Bicyclo[3.1.0]hexenes

Abstract

A practical air and moisture tolerant procedure for the preparation of 1,5-enynes from propargylic alcohols by the Brønsted acid catalyzed direct propargylic substitution of the hydroxy group with allylsilanes is described. Also, a straightforward sequential catalytic protocol for the synthesis of bicyclo[3.1.0]hexane derivatives, from readily available starting materials, is presented.

Key words

catalysis - allylations - alcohols - enynes - tandem reactions

References

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13

In some cases, and when refluxing conditions are required, competitive formation of the corresponding symmetric ether is observed (ca. 20% isolated yield).