Literature DB >> 25130870

N-heterocyclic carbene catalyzed formal [3+2] annulation reaction of enals: an efficient enantioselective access to spiro-heterocycles.

Chang Guo1, Michael Schedler, Constantin G Daniliuc, Frank Glorius.   

Abstract

A highly enantioselective N-heterocyclic carbene (NHC) catalyzed formal [3+2] annulation of α,β-unsaturated aldehydes with azaaurones or aurone generating spiro-heterocycles has been developed. The protocol represents a unique NHC-activation-based approach to access spiro-heterocyclic derivatives bearing a quaternary stereogenic center with high optical purity (up to 95% ee).
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; asymmetric synthesis; enals; organocatalysis; spiro-heterocycles

Year:  2014        PMID： 25130870     DOI： 10.1002/anie.201405381

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  14 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  A C1-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones.

Authors:  Jun-Bing Lin; Xi-Na Cheng; Xiao-Dong Tian; Guo-Qiang Xu; Yong-Chun Luo; Peng-Fei Xu
Journal:  RSC Adv       Date:  2018-04-24       Impact factor: 4.036

3.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

4.  Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.

Authors:  Qijian Ni; Xiaoxiao Song; Jiawen Xiong; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

5.  Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.

Authors:  C Guy Goodman; Morgan M Walker; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-12-23       Impact factor: 15.419

6.  N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.

Authors:  Xiang-Yu Chen; Kun-Quan Chen; De-Qun Sun; Song Ye
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

7.  A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones.

Authors:  Jian-Xiong An; Fen-Fen Yang; Pan Wang; Zhi-Cheng Gu; Yan Li; Lei Chen; Yong-Long Zhao; Bin He
Journal:  RSC Adv       Date:  2022-03-02       Impact factor: 3.361

8.  Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate.

Authors:  Huanzhen Ni; Zhaoyuan Yu; Weijun Yao; Yu Lan; Nisar Ullah; Yixin Lu
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

Review 9.  Recent Advances in the Synthesis of Spiroheterocycles via N-Heterocyclic Carbene Organocatalysis.

Authors:  Yue Liu; Xiang Zhang; Rong Zeng; Ying Zhang; Qing-Song Dai; Hai-Jun Leng; Xiao-Jun Gou; Jun-Long Li
Journal:  Molecules       Date:  2017-11-08       Impact factor: 4.411

10.  Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones.

Authors:  Xue Yan; Ying-De Tang; Cheng-Shi Jiang; Xigong Liu; Hua Zhang
Journal:  Molecules       Date:  2020-01-20       Impact factor: 4.411
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.