Formation of Tertiary Alcohols from the Rhodium-Catalyzed Reactions of Donor/Acceptor Carbenes with Esters

Liangbing Fu; Kevin Hoang; Cecilia Tortoreto; Wenbin Liu; Huw M L Davies

doi:10.1021/acs.orglett.8b00739

Formation of Tertiary Alcohols from the Rhodium-Catalyzed Reactions of Donor/Acceptor Carbenes with Esters

Org Lett. 2018 Apr 20;20(8):2399-2402. doi: 10.1021/acs.orglett.8b00739. Epub 2018 Apr 11.

Authors

Liangbing Fu¹, Kevin Hoang¹, Cecilia Tortoreto¹, Wenbin Liu¹, Huw M L Davies¹

Affiliation

¹ Department of Chemistry , Emory University , 1515 Dickey Drive , Atlanta , Georgia 30322 , United States.

PMID: 29641207
DOI: 10.1021/acs.orglett.8b00739

Abstract

Rhodium(II)-catalyzed reactions between isopropyl acetate and trichloroethyl aryldiazoacetates result in the formation of oxirane intermediates that ring open under the reaction conditions to form tertiary alcohols. When the reaction is catalyzed by the dirhodium tetrakis(triarylcyclopropanecarboxylate) complex, Rh₂( S-2-Cl,4-BrTPCP)₄, the tertiary alcohols are formed with good asymmetric induction (80-88% ee).

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't