One-Pot, Four-Step Organocatalytic Asymmetric Synthesis of Functionalized Nitrocyclopropanes

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• 作者：Anna Zaghi ; Tatiana Bernardi ; Valerio Bertolasi ; Olga Bortolini ; Alessandro Massi ; Carmela De Risi
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 18, 2015
• 年：2015
• 卷：80
• 期：18
• 页码：9176-9184
• 全文大小：536K
• ISSN：1520-6904

文摘

The asymmetric synthesis of functionalized nitrocyclopropanes has been achieved by a one-pot, four-step method catalyzed by (S)-diphenylprolinol TMS ether, which joins two sequential domino reactions, namely a domino sulfa-Michael/aldol condensation of 伪,尾-unsaturated aldehydes with 1,4-dithiane-2,5-diol, and a domino Michael/伪-alkylation reaction of the derived chiral dihydrothiophenes with bromonitromethane. The title compounds were obtained in 27鈥?5% yields, with high levels of diastereoselectivity (93:7 to 100:0 dr) and generally good enantioselectivities (up to 95:5 er).