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Catalytic Hydrogenolysis of Enantioenriched Donor–Acceptor Cyclopropanes Using H 2 and Palladium on Charcoal
Author(s) -
Sone Yoshitomo,
Kimura Yumi,
Ota Ryotaro,
Mochizuki Takehito,
Ito Junki,
Nishii Yoshinori
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.201700345
Subject(s) - hydrogenolysis , chemistry , cyclopropane , palladium , catalysis , enantiomeric excess , aryl , medicinal chemistry , enantiomer , organic chemistry , ring (chemistry) , enantioselective synthesis , stereochemistry , alkyl
The hydrogenolysis of enantioenriched donor–acceptor ( D–A ) cyclopropanes using H 2 (1 atm) and a catalytic amount of palladium on charcoal gave trans ‐α‐alkoxycarbonyl‐β‐benzyl‐γ‐lactones or β‐substituted γ‐aryl‐α,α‐diesters with high enantiomeric excess. The reaction was also used as a key step in the asymmetric total synthesis of yatein with high ee and excellent dr . This demonstrates the utility of this new protocol for the asymmetric synthesis of trans ‐α,β‐disubstituted γ‐butyrolactones. D–A cyclopropanes containing electron‐withdrawing groups at the β‐position were not susceptible to hydrogenolysis under these conditions. The reductive ring‐opening of a D–A cyclopropane using D 2 instead of H 2 generated the corresponding monodeuterated product.