Anti-Selective Asymmetric Nitro-Michael Reaction of Furanones: Diastereocontrol by Catalyst

详细信息    查看全文

• 作者：Tohru Sekikawa ; Takayuki Kitaguchi ; Hayato Kitaura ; Tatsuya Minami ; Yasuo Hatanaka
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：18
• 期：4
• 页码：646-649
• 全文大小：331K
• ISSN：1523-7052

文摘

Catalyst-controlled switching of diastereoselectivity from high syn-selectivity (>98/2 dr, syn) to anti-selectivity (up to 96/4 dr, anti) of the asymmetric nitro-Michael reaction of furanones is described. Anti-diastereoselectivity of the nitro-Michael reaction is very rare. With 0.1–5 mol % loadings of an epi-quinine catalyst, the reaction of 5-substituted 2(3H)-furanones with nitroalkenes smoothly proceeded to give the anti-Michael adducts in good yields (up to 95%) with excellent diastereo- and enantioselectivities (up to 96/4 dr, anti; up to 99% ee). DFT calculations support a model that accounts the high anti-diastereoselectivity.