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Copper catalyzed asymmetric propargylation of aldehydes.

Journal of the American Chemical Society (2010-05-21)
Daniel R Fandrick, Keith R Fandrick, Jonathan T Reeves, Zhulin Tan, Wenjun Tang, Andrew G Capacci, Sonia Rodriguez, Jinhua J Song, Heewon Lee, Nathan K Yee, Chris H Senanayake
PMID20481453
ABSTRACT

The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone.