Regioselective Allene Synthesis and Propargylations with Propargyl Diethanolamine Boronates
作者:Daniel R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake
DOI:10.1021/ol9022529
日期:2009.12.3
The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.