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Intriguing Electrophilic Reactivity of Donor–Acceptor Cyclopropanes: Experimental and Theoretical Studies
Author(s) -
Dousset Maxime,
Parrain JeanLuc,
Chouraqui Gaëlle
Publication year - 2017
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.201701058
Subject(s) - umpolung , chemistry , synthon , cyclopropane , nucleophile , stereocenter , reactivity (psychology) , electrophile , zwitterion , stereochemistry , acceptor , cyclopropanation , computational chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , molecule , ring (chemistry) , catalysis , medicine , physics , alternative medicine , pathology , condensed matter physics
A new reactivity of donor–acceptor cyclopropanes (DACs) has been highlighted and, for the first time, we report that they could formally behave as nucleophiles and be functionalized at their C3 position. The donor–acceptor cyclopropane acts as a formal nucleophilic synthetic equivalent of a 1,2‐zwitterion and could be described as an umpolung synthon. A highly substituted lactone is reached, and even more impressive is the formation of four stereogenic centers with complete control of their relative configuration. Both experimental and computational studies were performed to provide an overall picture of the mechanism.