Journal
ORGANIC LETTERS
Volume 24, Issue 29, Pages 5334-5338Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01976
Keywords
-
Categories
Funding
- Welch Foundation [E-1744]
- National Science Foundation [CHE-2102282]
Ask authors/readers for more resources
A chiral 6-substituted cyclohexenone was synthesized with high yields and enantioselectivities through a bisperfluorotoluyl-BINOL catalyzed conjugate addition of trifluoroborate salts to doubly vinylogous esters and aldol condensation. Stepwise and single-pot sequences were developed, with the former also providing beta-substituted masked ketoaldehydes containing a vinyl ether. This transformation was used in a four-step total synthesis of penienone with a significantly reduced number of steps compared to previous syntheses.
A bisperfluorotoluyl-BINOL catalyzed conjugate addition of trifluoroborate salts to doubly vinylogous esters and aldol condensation synthesized chiral 6-substituted cyclohexenones with high yields and enantioselectivities (10 examples, up to 89% yield, 89-98% ee). Stepwise and single-pot sequences were developed, with the former also providing beta-substituted masked ketoaldehydes containing a vinyl ether. The transformation was used in a four-step total synthesis of penienone (24% overall yield), <= half the steps as in previous syntheses.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available