Rhodium‐Catalyzed [4+2+1] Cycloaddition of In Situ Generated Ene/Yne‐Ene‐Allenes and CO | Zendy

Tian ZiYou | Zendy; Cui Qi | Zendy; Liu ChengHang | Zendy; Yu ZhiXiang | Zendy

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Rhodium‐Catalyzed [4+2+1] Cycloaddition of In Situ Generated Ene/Yne‐Ene‐Allenes and CO

Author(s) -

Tian ZiYou,

Cui Qi,

Liu ChengHang,

Yu ZhiXiang

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201805908

Subject(s) - ene reaction , cycloaddition , rhodium , chemistry , catalysis , in situ , medicinal chemistry , propargyl , stereochemistry , organic chemistry

Reported herein is the first rhodium‐catalyzed [4+2+1] cycloaddition of in situ generated ene/yne‐ene‐allenes and CO to synthesize challenging seven‐membered carbocycles fused with five‐membered rings. This reaction is designed based on the 1,3‐acyloxy migration of ene/yne‐ene‐propargyl esters to ene/yne‐ene‐allenes, followed by oxidative cyclization, CO insertion, and reductive elimination to form the final [4+2+1] cycloadducts. The possible competing [4+1], [4+2], and [2+2+1] cycloadditions were disfavored, making the present reaction an efficient way to access functionalized 5/7 rings.

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