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Rhodium‐Catalyzed Enantioselective Formal [4+1] Cycloaddition of Diazooxindoles and the Danishefsky Diene
Author(s) -
Cao Fei,
Hu Fang,
Xie QiMei,
Luo GaoYa,
Chu WenDao,
He Long,
Liu QuanZhong
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700639
Subject(s) - stereocenter , enantioselective synthesis , diene , cycloaddition , chemistry , rhodium , cyclopropanation , combinatorial chemistry , catalysis , formal synthesis , organic chemistry , stereochemistry , natural rubber
Optically enriched cyclopentenones are synthetically versatile molecules, and their rapid and efficient straightforward assembly from simple starting materials is highly desired. Herein, we report a rhodium‐catalyzed enantioselective formal [4+1] cycloaddition of diazooxindoles and the Danishefsky diene. The formation of cyclopentenones proceeds via ring expansion of the vinylcyclopropanes formed in situ via cyclopropanation. The optically and highly structurally enriched indoline spirocyclopentenone bearing an all‐carbon stereocenter was formed in a one‐pot, two‐step manner in good to excellent yields and enantioselectivities (up to 90 % ee ).