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

共 50 条

[31] One-pot synthesis of substituted steroidal thiazoles
Shafiullah, S
Siddiqui, IH
Jamaluddin, M
Khan, EH
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2000, 77 (02) : 102 - 103
[32] One-Pot Synthesis and Hydrolysis Behavior of Highly Water-Soluble Ammonium Polyphosphate
Wang, Baoming
Lv, Zhonghao
Yu, Mengmeng
Liu, Xu
Li, Cuili
Hua, Quanxian
Liu, Yong
Liu, Pengfei
Shen, Bo
Zhao, Nan
Ding, Junxiang
Tang, Jianwei
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2022, 10 (39) : 13037 - 13049
[33] Ammonium acetate mediated simple, rapid, and one-pot multicomponent synthesis of spirooxindole derivatives
Raheja, Barkha K.
Dalal, Dipak S.
SYNTHETIC COMMUNICATIONS, 2023, 53 (11) : 808 - 822
[34] A One-Pot Synthesis of Highly Functionalized Purines
Zelli, Renaud
Zeinyeh, Wael
Haudecoeur, Romain
Alliot, Julien
Boucherle, Benjamin
Callebaut, Isabelle
Decout, Jean-Luc
ORGANIC LETTERS, 2017, 19 (23) : 6360 - 6363
[35] Highly efficient one-pot synthesis of tetrahydropyridines
Ramin, Ghorbani-Vaghei
Hajar, Shahbazi
COMPTES RENDUS CHIMIE, 2013, 16 (11) : 1047 - 1054
[36] One-Pot Synthesis of Highly Substituted Quinolines in Aqueous Medium and Its Application for the Synthesis of Azalignans
Kumar, Amrendra
Prajapati, Rmanand
Kant, Ruchir
Narender, Tadigoppula
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (34) : 5551 - 5556
[37] A novel one pot synthesis of γ-butyrolactones
Reddy, GS
Neelakantan, P
Iyengar, DS
SYNTHETIC COMMUNICATIONS, 2002, 32 (17) : 2601 - 2604
[38] Tin Powder-Promoted "One-Pot" Synthesis of α-Methylene-γ-butyrolactones
Yang, Zheng
Huang, Danfeng
Wen, Lan
Wang, Juanjuan
Wang, Kehu
Hu, Yulai
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (07) : 1725 - 1732
[39] An Efficient One-Pot Synthesis of Highly Substituted Pyridone Derivatives and Their Antimicrobial and Antifungal Activity
Pandit, Archana B.
Savant, Mahesh M.
Ladva, Kartik D.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (04) : 983 - 987
[40] MULTICOMPONENT, ONE-POT SYNTHESIS OF HIGHLY SUBSTITUTED PYRIDINES WITH ZINC OXIDE NANOPARTICLES AS CATALYST
Patil, Kiran
Kumbhar, Deepak
Patil, Amol
Karhale, Shrikrishna
Helavi, Vasant
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 27 (02) : 157 - 164

← 1 2 3 4 5 →