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Rh I ‐Catalyzed Carbonylative [3+1] Construction of Cyclobutenones via C−C σ‐Bond Activation of Cyclopropenes
Author(s) -
Xu WenBin,
Li Changkun,
Wang Jianbo
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804170
Subject(s) - catalysis , chemistry , cycloaddition , medicinal chemistry , double bond , chelation , organic chemistry
With a catalytic amount of Rh(cod) 2 BF 4 and dppm, cyclopropenes undergo a direct carbonylative [3+1] cycloaddition reaction under an atmosphere of CO to produce the cyclobutenones in excellent yields, in which the regio‐ and diastereoselectivities can be controlled in certain cases with the help of chelating groups. Cyclobutenone with a chiral 4‐position was prepared by diastereoselective induction. Rhodacyclopentenone has been determined as the key intermediate, as it was synthesized and applied to the reductive elimination step.