Literature DB >> 27378106

Phosphine-Catalyzed [2 + 4] Annulation of Allenoates with Thiazolone-Derived Alkenes: Synthesis of Functionalized 6,7-Dihydro-5H-pyrano[2,3-d]thiazoles.

Chang Wang1, Zhenzhen Gao1, Leijie Zhou1, Chunhao Yuan1, Zhanhu Sun1, Yumei Xiao1, Hongchao Guo1.   

Abstract

Phosphine-catalyzed [2 + 4] annulation of allenoates with thiazolone-derived alkenes has been achieved under mild conditions, giving biologically important 6,7-dihydro-5H-pyrano[2,3-d]thiazole derivatives in high to excellent yields. With the use of Kwon's phosphine as the chiral catalyst, optically active products were obtained in good yields with excellent enantioselectivities.

Entities:  

Year:  2016        PMID: 27378106     DOI: 10.1021/acs.orglett.6b01571

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


  5 in total

1.  Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.

Authors:  Andrew J Smaligo; Sriramurthy Vardhineedi; Ohyun Kwon
Journal:  ACS Catal       Date:  2018-05-04       Impact factor: 13.084

Review 2.  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

3.  Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.

Authors:  Andreas Eitzinger; Katharina Zielke; Michael Widhalm; Raphaël Robiette; Mario Waser
Journal:  Asian J Org Chem       Date:  2018-05-04       Impact factor: 3.319

4.  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

5.  Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines.

Authors:  Huamin Wang; Xiuzheng Li; Youshao Tu; Junliang Zhang
Journal:  iScience       Date:  2020-05-06
  5 in total

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