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Divergent Phosphine‐Catalyzed [2+4] or [3+2] Cycloaddition Reactions of γ‐Substituted Allenoates with Oxadienes
Author(s) -
Li Erqing,
Chang Meijia,
Liang Ling,
Huang You
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403369
Subject(s) - dihydropyran , chemistry , phosphine , catalysis , synthon , cycloaddition , cyclopentene , domino , organic chemistry , cascade reaction , combinatorial chemistry , medicinal chemistry
A strategy was developed to construct dihydropyran and multifunctional cyclopentene derivatives from the same starting materials by using different phosphine catalysts. By exploiting the different nucleophilicities of the phosphine catalysts, the γ‐substituted allenoates selectively acted as C 3 or C 2 synthons. Under the catalysis of different organophosphine catalysts, the domino reaction proceeded smoothly with broad substrate tolerance and excellent total yields. The results suggest that the ethyl group of the γ‐substituted allenoates played a key role in the domino reaction.