Literature DB >> 26506021

N-Heterocyclic Carbene-Catalyzed Formal [3 + 2] Annulation of α-Bromoenals with 3-Aminooxindoles: A Stereoselective Synthesis of Spirooxindole γ-Butyrolactams.

Delu Jiang1, Shuding Dong1, Weifang Tang1, Tao Lu1, Ding Du1.   

Abstract

A stereoselective synthetic approach to spirooxindole γ-butyrolactams is developed via N-heterocyclic carbene-catalyzed formal [3 + 2] annulation of α-bromoenals with 3-aminooxindoles. An enantioselective variant of this methodology is also investigated resulting in good substrate tolerance and high enantioselectivities.

Entities:  

Year:  2015        PMID: 26506021     DOI: 10.1021/acs.joc.5b02188

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 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.  A formal intermolecular [4 + 1] cycloaddition reaction of 3-chlorooxindole and o-quinone methides: a facile synthesis of spirocyclic oxindole scaffolds.

Authors:  Chao Lin; Qi Xing; Honglei Xie
Journal:  RSC Adv       Date:  2021-05-24       Impact factor: 4.036

3.  Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles.

Authors:  Ziwei Zhong; Zhijie Xiao; Xiaohua Liu; Weidi Cao; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

Review 4.  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

5.  Iodide/H₂O₂ Catalyzed Intramolecular Oxidative Amination for the Synthesis of 3,2'-Pyrrolidinyl Spirooxindoles.

Authors:  Yu-Ting Gao; Xiao-Yang Jin; Qi Liu; An-Di Liu; Liang Cheng; Dong Wang; Li Liu
Journal:  Molecules       Date:  2018-09-05       Impact factor: 4.411

  5 in total

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