Literature DB >> 26359687

[4 + 3] Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides.

Gu Zhan1, Ming-Lin Shi1, Qing He1, Wei Du1, Ying-Chun Chen1,2.   

Abstract

Efficient construction of a challenging aza-spirocycloheptane oxindole scaffold is reported through an unprecedented [4 + 3] cycloaddition reaction with bromo-substituted Morita-Baylis-Hillman adducts of isatins and N-(ortho-chloromethyl)aryl amides. Both reactive intermediates, the allylic phosphonium ylides and aza-o-quinone methides, were in situ generated, chemoselectively facilitated by a Lewis base and Brønsted base, respectively.

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Year:  2015        PMID: 26359687     DOI: 10.1021/acs.orglett.5b02279

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.

Authors:  Kui Zhang; Lingchao Cai; Sooji Hong; Ohyun Kwon
Journal:  Org Lett       Date:  2019-06-20       Impact factor: 6.005

3.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

4.  Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones.

Authors:  Guipeng Feng; Guoyang Ma; Wenyan Chen; Shaohong Xu; Kaikai Wang; Shaoyan Wang
Journal:  Molecules       Date:  2021-05-17       Impact factor: 4.411

5.  Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.

Authors:  Yang Zheng; Ping Dai; Dafang Gao; Kemiao Hong; Luyao Kou; Shanliang Dong; Jundie Hu; Lihua Qiu; Wenhao Hu; Xiaoguang Bao; Xinfang Xu
Journal:  iScience       Date:  2020-05-15
  5 in total

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