Copper(I)-catalyzed substitution of propargylic carbonates with diboron: selective synthesis of multisubstituted allenylboronates.

Abstract

A versatile synthetic method for the preparation of the allenylboronates, Cu(I)-catalyzed reaction of propargylic carbonates with a diboron, is described. A Cu(O-t-Bu)-Xantphos catalyst system was effective for the preparation of various allenylboron compounds, allenylboronates with different substitution patterns, those with functional groups, and an axially chiral one. The Lewis acid promoted stereoselective addition to aldehydes leading to homopropargylic alcohols showed the usefulness of the new allenylboronates.

DOI: 10.1021/ja806602h

1 Figure or Table

Cite this paper

@article{Ito2008CopperIcatalyzedSO, title={Copper(I)-catalyzed substitution of propargylic carbonates with diboron: selective synthesis of multisubstituted allenylboronates.}, author={Hajime Ito and Yusuke Sasaki and Masaya Sawamura}, journal={Journal of the American Chemical Society}, year={2008}, volume={130 47}, pages={15774-5} }