Diversified Cycloisomerization/Diels-Alder Reactions of 1,6-Enynes through Bimetallic Relay Asymmetric Catalysis

Haifeng Zheng; Yan Wang; Chaoran Xu; Qian Xiong; Lili Lin; Xiaoming Feng

doi:10.1002/anie.201900421

Diversified Cycloisomerization/Diels-Alder Reactions of 1,6-Enynes through Bimetallic Relay Asymmetric Catalysis

Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5327-5331. doi: 10.1002/anie.201900421. Epub 2019 Mar 4.

Authors

Haifeng Zheng¹, Yan Wang¹, Chaoran Xu¹, Qian Xiong¹, Lili Lin¹, Xiaoming Feng¹

Affiliation

¹ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.

PMID: 30758902
DOI: 10.1002/anie.201900421

Abstract

We report the combination of transition-metal-catalyzed diversified cycloisomerization of 1,6-enynes with chiral Lewis acid promoted asymmetric Diels-Alder reaction to realize asymmetric cycloisomerization/Diels-Alder relay reactions of 1,6-enynes with electron-deficient alkenes. A broad spectrum of chiral [5,6]-bicyclic products could be acquired in high yields (up to 99 %) with excellent diastereoselectivy (>19:1 dr) and enantioselectivity (up to 99 % ee).

Keywords: 1,6-enynes; Diels-Alder reactions; asymmetric catalysis; bimetallic catalysis; cycloisomerization.

Abstract

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