Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substitutedγ-Butyrolactones

被引：13
作者：
Drennhaus, Till [2 ]
Oehler, Laura [1 ]
Djalali, Saveh [1 ]
Hoefmann, Svenja [1 ]
Mueller, Clemens [1 ]
Pietruszka, Joerg [1 ,2 ]
Worgull, Dennis [1 ]
机构：
[1] Heinrich Heine Univ Dusseldorf, Forschungszentrum Julich, Inst Bioorgan Chem, Stetternicher Forst, Bldg 15-8, D-52426 Julich, Germany
[2] Forschungszentrum Julich, Inst Bio & Geosci IBG 1, D-52426 Julich, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 12期
关键词：
asymmetric synthesis; asymmetric catalysis; heterocycles; lactones; multicomponent reactions; ylides; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CINCHONA ALKALOIDS; DIASTEREOSELECTIVE SYNTHESIS; FACILE SYNTHESIS; 4+1 ANNULATION; EFFICIENT; DERIVATIVES; CYCLOPROPANATION; QUATERNARY;
D O I：
10.1002/adsc.202000039
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An ammonium ylide mediated access towardstrans-beta,gamma-disubstituted,all-trans-alpha,beta,gamma-trisubstituted, and alpha,alpha,beta,gamma-tetrasubstituted gamma-butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and alpha-bromo carbonyl compounds,gamma-butyrolactones were obtained in yields between 32-99% with up to excellent diastereoselectivities (>95:5)viaa DABCO-mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R, 4R)-beta,gamma-disubstituted and (2R, 3R, 4R)-alpha,beta,gamma-trisubstituted gamma-butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration.
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收藏
页码：2385 / 2396
页数：12
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