Hao Yu, Li Zi-Hao, Lian Peng-Fei, Li Quan-Zhe, She Yuan, Ma Zhi-Gang, Zhang Shu-Yu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China.
Key Laboratory of Green and High-value Utilization of Salt Lake Resources, Qinghai Institute of Salt Lakes, Chinese Academy of Sciences, Xining 810008, China.
Org Lett. 2023 Sep 22;25(37):6913-6918. doi: 10.1021/acs.orglett.3c02690. Epub 2023 Sep 11.
Herein, we describe a stereoselective sulfa-Michael/aldol cyclization reaction promoted by a rationally designed novel axially chiral styrene-based organocatalyst. A variety of highly substituted tetrahydrothiophenes featuring an alkyne-substituted quaternary stereogenic center are obtained in good yields, excellent stereoselectivities, and exclusive selectivities. This process tolerates a broad range of alkynyl-substituted acrylamides under mind conditions. The utility of this approach is highlighted in its excellent asymmetric introduction, scalability, and attractive product diversification.
在此，我们描述了一种由合理设计的新型轴向手性苯乙烯基有机催化剂促进的立体选择性硫醇-迈克尔/羟醛环化反应。以良好的产率、优异的立体选择性和专一的选择性得到了多种具有炔基取代季碳立体中心的高度取代四氢噻吩。该过程在温和条件下能耐受多种炔基取代的丙烯酰胺。这种方法的实用性体现在其出色的不对称引入、可扩展性和诱人的产物多样性上。
