Zaghi Anna, Bernardi Tatiana, Bertolasi Valerio, Bortolini Olga, Massi Alessandro, De Risi Carmela
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara , Via Fossato di Mortara 17, 44121 Ferrara, Italy.
J Org Chem. 2015 Sep 18;80(18):9176-84. doi: 10.1021/acs.joc.5b01607. Epub 2015 Sep 9.
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).
通过由（S）-二苯基脯氨醇TMS醚催化的一锅四步法实现了功能化硝基环丙烷的不对称合成，该方法结合了两个连续的多米诺反应，即α，β-不饱和醛与1,4-二硫杂环乙烷-2,5-二醇的多米诺硫醚-迈克尔/羟醛缩合反应，以及衍生的手性二氢噻吩与溴硝基甲烷的多米诺迈克尔/α-烷基化反应。标题化合物的产率为27-45%，具有高水平的非对映选择性（93:7至100:0 dr），并且通常具有良好的对映选择性（高达95:5 er）。
