Literature DB >> 28398445

Enantioselective [4 + 1] cycloaddition of ortho-quinone methides and bromomalonates under phase-transfer catalysis.

Xiao-Lei Lian1, Alafate Adili, Bin Liu, Zhong-Lin Tao, Zhi-Yong Han.   

Abstract

An enantioselective [4 + 1] cycloaddition reaction of ortho-quinone methides and bromomalonates using a quinine and BINOL derived phase-transfer catalyst is described. With high yields and enantioselectivities, the method provided a variety of optically active dihydrobenzofurans, which represent a valuable structural motif present in numerous naturally occurring and biologically active molecules.

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Year:  2017        PMID: 28398445     DOI: 10.1039/c7ob00484b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.

Authors:  Katharina Zielke; Mario Waser
Journal:  Org Lett       Date:  2018-01-19       Impact factor: 6.005

2.  Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides.

Authors:  Lukas Roiser; Mario Waser
Journal:  Org Lett       Date:  2017-04-20       Impact factor: 6.005

3.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

4.  Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates.

Authors:  Katharina Zielke; Ondřej Kováč; Michael Winter; Jiří Pospíšil; Mario Waser
Journal:  Chemistry       Date:  2019-05-21       Impact factor: 5.236

5.  Phosphine-mediated enantioselective [1 + 4]-annulation of Morita-Baylis-Hillman carbonates with 2-enoylpyridines.

Authors:  Tao Wang; Pengfei Zhang; Wenjun Li; Pengfei Li
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 3.361

6.  Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles.

Authors:  Jing-Wen Kang; Xiang Li; Fei-Yu Chen; Yuan Luo; Shu-Cang Zhang; Bin Kang; Cheng Peng; Xu Tian; Bo Han
Journal:  RSC Adv       Date:  2019-04-17       Impact factor: 4.036

  6 in total

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