1,2-二取代硫代环丁烷的对映选择性合成：迈克尔加成反应

Robert Emma G L, Waser Jerome

Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland

Chem Sci. 2025 May 23;16(26):12115-12121. doi: 10.1039/d5sc01727k. eCollection 2025 Jul 2.

We report the diastereoselective and enantioselective synthesis of thio-substituted cyclobutanes a sulfa-Michael addition using cyclobutenes. In the presence of DBU, various thio-cyclobutane esters and amides were obtained in up to quantitative yield and >95 : 5 dr. Using a chiral chinchona-based squaramide bifunctional acid-base catalyst and an -acyl-oxazolidinone-substituted cyclobutene, thio-cyclobutanes were obtained with high yield and enantioselectivity (er up to 99.7 : 0.3).

我们报道了使用环丁烯通过硫代迈克尔加成反应实现硫代取代环丁烷的非对映选择性和对映选择性合成。在DBU存在下，以高达定量的产率和>95:5的非对映体比例获得了各种硫代环丁烷酯和酰胺。使用基于金鸡纳碱的手性方酰胺双功能酸碱催化剂和酰基恶唑烷酮取代的环丁烯，以高产率和对映选择性（对映体比例高达99.7:0.3）获得了硫代环丁烷。