Catalytic stereoselective synthesis of cyclopentanones from donor-acceptor cyclopropanes and in situ-generated ketenes

被引：1
|
作者：
Mitra, Shubhanjan [1 ,2 ]
Connolly, Sophie M. [1 ,2 ]
Ayidi, Saud [1 ,2 ]
Mondal, Mukulesh [3 ]
Panda, Manashi [3 ]
Kelly, Brian G. [4 ]
Kerrigan, Nessan J. [1 ,2 ]
机构：
[1] Dublin City Univ, Sch Chem Sci, Dublin, Ireland
[2] Dublin City Univ, Life Sci Inst, Dublin, Ireland
[3] Oakland Univ, Dept Chem, 2200 N Squirrel Rd, Rochester, MI 48309 USA
[4] KelAda Pharmachem, Dublin, Ireland
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 35期
基金：
爱尔兰科学基金会;
关键词：
ENOL SILYL ETHERS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; 3+2 ANNULATION; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; BETA-LACTONES; BRONSTED ACID; CYCLOADDITION; CONSTRUCTION;
D O I：
10.1039/d4ob01313a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A dual InBr3-EtAlCl2 Lewis acidic system was found to be optimal for promoting the diastereoselective (3 + 2)-cycloaddition of donor-acceptor cyclopropanes with in situ-generated ketenes to form cyclopentanones. The desired products were formed in good to excellent yields (70-93% for 16 examples) and with good to excellent diastereoselectivity and enantiospecificity.
引用
收藏
页码：7128 / 7132
页数：5
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