Title | Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones. |
Publication Type | Journal Article |
Year of Publication | 2018 |
Authors | Lee J, Wang S, Callahan M, Nagorny P |
Journal | Org Lett |
Volume | 20 |
Issue | 7 |
Pagination | 2067-2070 |
Date Published | 2018 Apr 06 |
ISSN | 1523-7052 |
Abstract | This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β'-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials. |
DOI | 10.1021/acs.orglett.8b00607 |
Alternate Journal | Org. Lett. |
PubMed ID | 29560721 |
PubMed Central ID | PMC5889748 |
Grant List | R01 GM111476 / GM / NIGMS NIH HHS / United States |
Submitted by kej2006 on June 6, 2018 - 4:13pm