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.

引用

页码：2385 / 2396

页数：12

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