Literature DB >> 20936854

"One-pot" access to 4H-chromenes with formation of a chiral quaternary stereogenic center by a highly enantioselective iminium-allenamine involved oxa-Michael-aldol cascade.

Chunliang Liu1, Xinshuai Zhang, Rui Wang, Wei Wang.   

Abstract

An unprecedented organocatalytic highly enantioselective cascade Michael-aldol reaction has been developed in high yields under mild reaction conditions. The "one-pot" process affords an efficient approach to the synthetically and biologically important chiral 4H-chromenes bearing a quaternary stereogenic center. The study significantly expands the scope of less explored organocatalytic iminium-allenamine chemistry.

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Year:  2010        PMID: 20936854     DOI: 10.1021/ol102096s

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


  4 in total

1.  Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Authors:  Kerem E Ozboya; Tomislav Rovis
Journal:  Chem Sci       Date:  2011-09-01       Impact factor: 9.825

2.  Organocatalytic atroposelective synthesis of axially chiral styrenes.

Authors:  Sheng-Cai Zheng; San Wu; Qinghai Zhou; Lung Wa Chung; Liu Ye; Bin Tan
Journal:  Nat Commun       Date:  2017-05-03       Impact factor: 14.919

3.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

4.  Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines.

Authors:  Chittaranjan Bhanja; Satyaban Jena; Sabita Nayak; Seetaram Mohapatra
Journal:  Beilstein J Org Chem       Date:  2012-10-04       Impact factor: 2.883

  4 in total

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