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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201805908
Subject(s) - ene reaction , cycloaddition , rhodium , chemistry , catalysis , medicinal chemistry , allene , in situ , propargyl , 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.