Literature DB >> 30829043

Palladium-Catalyzed Highly Enantioselective Cycloaddition of Vinyl Cyclopropanes with Imines.

Xiao-Bing Huang1, Xian-Jing Li1, Tian-Tian Li1, Bo Chen1, Wen-Dao Chu1, Long He1,2, Quan-Zhong Liu1.   

Abstract

Palladium-catalyzed asymmetric formal [3 + 2] cycloaddition of vinyl cyclopropanes and aldimines or isatin-derived ketimines proceeded smoothly in the presence of chiral phosphoramidite ligands. The corresponding highly functionalized and optically enriched pyrrolidine or spiro[pyrrolidin-3,2'-oxindole] derivatives are obtained in up to 94% yield and with up to 96% ee and 7:1 dr.

Entities:  

Year:  2019        PMID: 30829043     DOI: 10.1021/acs.orglett.9b00274

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


  5 in total

1.  Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Authors:  Hongmei Qin; Qimei Xie; Long He
Journal:  RSC Adv       Date:  2022-06-06       Impact factor: 4.036

2.  Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes.

Authors:  Matteo Faltracco; Koen N A van de Vrande; Martijn Dijkstra; Jordy M Saya; Trevor A Hamlin; Eelco Ruijter
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-26       Impact factor: 15.336

3.  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

4.  Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Authors:  Jianhua Wang; Stephanie A Blaszczyk; Xiaoxun Li; Weiping Tang
Journal:  Chem Rev       Date:  2020-08-05       Impact factor: 72.087

5.  Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols.

Authors:  Hua Zhao; Peng Shen; Dongru Sun; Hongbin Zhai; Yufen Zhao
Journal:  Front Chem       Date:  2021-07-16       Impact factor: 5.221

  5 in total

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