Literature DB >> 15839655

Enantioselective addition of nitrones to activated cyclopropanes.

Mukund P Sibi1, Zhihua Ma, Craig P Jasperse.   

Abstract

In this paper, we demonstrate the first examples of chiral Lewis acid catalysis in the formation of tetrahydro-1,2-oxazines with very high enantioselectivity starting with diactivated cyclopropanes and nitrones (>90% yields and ee). Reactions with racemic substituted cyclopropanes provide approximately 1:1 diastereomeric tetrahydro-1,2-oxazine products with high enantioselectivity. Mechanistic information for the formation of the tetrahydro-1,2-oxazines is also detailed.

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Year:  2005        PMID: 15839655     DOI: 10.1021/ja0421497

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Enantioselective Radical Reactions. Formation of Chiral Quaternary Centers.

Authors:  Mukund P Sibi; Liwen He
Journal:  Synlett       Date:  2006-03       Impact factor: 2.454

2.  Highly diastereo- and enantioselective additions of homoenolates to nitrones catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-31       Impact factor: 15.419

Review 3.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

4.  One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors:  Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal:  Org Lett       Date:  2015-08-07       Impact factor: 6.005

5.  Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines.

Authors:  Hongchao Guo; Qihai Xu; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

6.  Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes.

Authors:  Johannes Preindl; Shyamal Chakrabarty; Jérôme Waser
Journal:  Chem Sci       Date:  2017-08-25       Impact factor: 9.825

7.  A novel type of donor-acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls.

Authors:  Haidong Liu; Lifang Tian; Hui Wang; Zhi-Qiang Li; Chi Zhang; Fei Xue; Chao Feng
Journal:  Chem Sci       Date:  2022-02-15       Impact factor: 9.825

8.  Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines.

Authors:  Reinhold Zimmer; Elmar Schmidt; Michal Andrä; Marcel-Antoine Duhs; Igor Linder; Hans-Ulrich Reissig
Journal:  Beilstein J Org Chem       Date:  2009-09-16       Impact factor: 2.883

9.  Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones.

Authors:  Peng-Wei Xu; Jia-Kuan Liu; Lan Shen; Zhong-Yan Cao; Xiao-Li Zhao; Jun Yan; Jian Zhou
Journal:  Nat Commun       Date:  2017-11-20       Impact factor: 14.919

  9 in total

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