Literature DB >> 21088771

Enantioselective organocatalytic domino Michael-acetalization-Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones.

Bor-Cherng Hong1, Prakash Kotame, Ju-Hsiou Liao.   

Abstract

Asymmetric domino Michael-acetalization reactions of 2-hydroxynitrostyrene and aldehydes "on water" followed by oxidation providing the cis-3,4-disubstituted dihydrocoumarins with excellent enantioselectivities (up to >99% ee). The variant with glutaraldehyde underwent a highly stereoselective domino Michael-acetalization-Henry reaction to afford the tetrahydro-6H-benzo[c]chromen-6-ones after the subsequent oxidation.

Entities:  

Year:  2010        PMID: 21088771     DOI: 10.1039/c0ob00834f

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


  3 in total

1.  Diastereodivergent Synthesis of Hexahydro-6H-benzo[c]chromen-6-one Derivatives Catalyzed by Modularly Designed Organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; Hadi D Arman; John C-G Zhao
Journal:  Chemistry       Date:  2019-05-09       Impact factor: 5.236

2.  Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts.

Authors:  Satish Jakkampudi; Ramarao Parella; John C-G Zhao
Journal:  Org Biomol Chem       Date:  2018-12-19       Impact factor: 3.876

3.  A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates.

Authors:  Hong-Bo Zhang; Yong-Chun Luo; Xiu-Qin Hu; Yong-Min Liang; Peng-Fei Xu
Journal:  Beilstein J Org Chem       Date:  2016-02-11       Impact factor: 2.883

  3 in total

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