Journal
ORGANIC LETTERS
Volume 24, Issue 48, Pages 8816-8820Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03551
Keywords
-
Categories
Funding
- Natural Science Foundation of Zhejiang Province (ZJNSF)
- [LY19B020005]
Ask authors/readers for more resources
A rhodium-catalyzed highly enantio- and diaster-eoselective alkenylation reaction of Ay-unsaturated butenolides is reported. The use of a chiral diene ligand enables the synthesis of chiral butyrolactones in high yields with extremely high enantioselectivities and high diastereoselectivities. The key process involves the isomerization of butenolides and subsequent dynamic kinetic resolution.
A rhodium-catalyzed highly enantio- and diaster-eoselective alkenylation of Ay-unsaturated butenolides is reported. The use of a chiral diene ligand, (S,S)-Ph-bod, enables the facile synthesis of chiral butyrolactones in high yields with extremely high enantioselectivities (>99% ee in all cases) and high diastereoselectivities (up to >20:1 dr). The key process of the reaction involves the isomerization of beta,gamma-unsaturated butenolides to racemic alpha,beta-unsaturated butenolides and the subsequent dynamic kinetic resolution through ligand-controlled, enantio-selective alkenylation with an alkenylrhodium species that is generated in situ via 1,4-rhodium migration.
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