Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes via in Situ Generated Chiral Fluoride-Catalyzed Cascade Sulfa-Michael/Aldol Reaction of 1,4-Dithiane-2,5-diol and α,β-Unsaturated Ketones

被引：42
|
作者：
Duan, Mengying [1 ]
Liu, Yidong [1 ]
Ao, Jun [1 ]
Xue, Lu [1 ]
Luo, Shilong [1 ]
Tan, Yu [1 ]
Qin, Wenling [1 ]
Song, Choong Eui [2 ]
Yan, Hailong [1 ]
机构：
[1] Chongqing Univ, Sch Pharmaceut Sci, IDRC, Chongqing 401331, Peoples R China
[2] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 09期
关键词：
CATION-BINDING CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; FACILE SYNTHESIS; DERIVATIVES; STEREOCENTERS; CONSTRUCTION; ALCOHOLS; BEARING; ION;
D O I：
10.1021/acs.orglett.7b00813
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chiral, fluoride-catalyzed asymmetric cascade sulfaMichael/aldol condensation reaction of 1,4-dithiane-2,5-diol and a series of alpha,beta-unsaturated ketones is described to access chiral trisubstituted tetrahydrothiophene derivatives. The target products, including the spiro tetrahydrothiophene derivatives bearing a five-, six-, and seven-membered ring, were highly functionalized and showed high ee value. This established protocol realized a highly enantioselective reaction with a catalytic amount of KF and Song's chiral oligoEG via in situ generated chiral fluoride to construct useful heterocyclic skeletons with great complexity.
引用
收藏
页码：2298 / 2301
页数：4
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