Synlett 2020; 31(18): 1741-1746
DOI: 10.1055/s-0040-1707190
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© Georg Thieme Verlag Stuttgart · New York

Synergistic Catalysis for Stereodivergent Synthesis of trans- and cis-Skipped Dienes

Fang Wang
,
Shenqqing Zhu
,
Lingling Chu
We thank the National Natural Science Foundation of China (21971036, 21901036, 21702029), the Shanghai Sailing Program (19YF1400300), and the Fundamental Research Funds for the Central Universities for financial support.
Further Information

Publication History

Received: 02 June 2020

Accepted after revision: 12 June 2020

Publication Date:
14 July 2020 (online)


Abstract

Catalytic, stereoselective synthesis of skipped dienes is an important topic in organic synthesis. Summarized here are the transition-metal-catalyzed stereoselective approaches and a new, photoinduced stereodivergent strategy reported by our group recently. Our strategy utilizes a synergistic photoredox/nickel protocol to enable the cross-electrophile coupling of allylic carbonates and vinyl triflates to construct 1,4-dienes, the stereoselectivity of which was tuned by the triplet energy (E T) photocatalysts employed, offering a convenient and stereodivergent solution to (E)- and (Z)-1,4-dienes from one set of substrates.