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

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• 作者：Guang-Fen Du ; Xiao-Lei Zou ; Bin Dai ; Lin He ; ^{helin@shzu.edu.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：N-heterocyclic carbenes ; 3-Trimethylsilyl propiolate ; Alkynylation ; β-Branched Morita&ndash ; Baylis&ndash ; Hillman adducts
• 刊名：Journal of Saudi Chemical Society
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：20
• 期：2
• 页码：207-212
• 全文大小：1836 K

文摘

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, β-naphthaldehyde, meta- and para-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford β-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.