N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes

Abstract EN

A N-heterocyclic carbene (NHC) catalyzed addition reaction of 3-trimethylsilyl propiolate with aldehydes has been developed.

Under the catalysis of 2 mol% NHCs, benzaldehyde, furfural, b-naphthaldehyde, meta- and para-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford b-acylated MBH adducts in good yield with excellent stereoselectivity.

While ortho-substituted benzaldehydes coupled with 3-trimethylsilyl propiolate to give alkynylation products as the sole products under the same reaction conditions.