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One-Pot, Four-Step Organocatalytic Asymmetric Synthesis of Functionalized Nitrocyclopropanes. 2015
Anna Zaghi, and
Tatiana Bernardi, and
Valerio Bertolasi, and
Olga Bortolini, and
Alessandro Massi, and
Carmela De Risi
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara , Via Fossato di Mortara 17, 44121 Ferrara, Italy.
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 α,β-unsaturated aldehydes with 1,4-dithiane-2,5-diol, and a domino Michael/α-alkylation reaction of the derived chiral dihydrothiophenes with bromonitromethane. The title compounds were obtained in 27-45% yields, with high levels of diastereoselectivity (93:7 to 100:0 dr) and generally good enantioselectivities (up to 95:5 er).
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