Literature DB >> 25689040

An NHC-catalyzed in situ activation strategy to β-functionalize saturated carboxylic acid: an enantioselective formal [3+2] annulation for spirocyclic oxindolo-γ-butyrolactones.

Yuanwei Xie1, Chenxia Yu, Tuanjie Li, Shujiang Tu, Changsheng Yao.   

Abstract

An in situ NHC-catalyzed activation strategy to β-functionalize saturated carboxylic acid was developed. This asymmetric formal [3+2] annulation could deliver spirocyclic oxindolo-γ-butyrolactones from saturated carboxylic acid and isatin in good yields with high to excellent enantioselectivities. The easy availability of the starting materials, direct installation of functional units at unreactive carbon atom and the convergent assembly make this protocol attractive in the field of organic synthesis.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbine; annulation; beta-functionalization; organocatalysis; spirocyclic oxindole

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Year:  2015        PMID: 25689040     DOI: 10.1002/chem.201500345

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

Review 1.  Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity.

Authors:  Mei-Mei Li; Xiaozhen Chen; Yun Deng; Jun Lu
Journal:  RSC Adv       Date:  2021-11-26       Impact factor: 4.036

2.  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

Review 3.  A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones.

Authors:  Joonseong Hur; Jaebong Jang; Jaehoon Sim
Journal:  Int J Mol Sci       Date:  2021-03-09       Impact factor: 5.923

  3 in total

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