Rhodium-Catalyzed Highly Enantio- and Diastereoselective Alkenylation of β,γ-Unsaturated Butenolides via Dynamic Kinetic Resolution

被引：3
|
作者：
Lu, Xiaosa [2 ]
Zhu, Jie [2 ]
Huang, Yinhua [1 ]
机构：
[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Peoples R China
[2] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 48期
关键词：
CHIRAL DIENE LIGANDS; ASYMMETRIC-SYNTHESIS; BOND; ARYLATION; PALLADIUM;
D O I：
10.1021/acs.orglett.2c03551
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：8816 / 8820
页数：5
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