Literature DB >> 22409456

BINAPHANE-catalyzed asymmetric synthesis of trans-β-lactams from disubstituted ketenes and N-tosyl arylimines.

Shi Chen1, Eric C Salo, Kraig A Wheeler, Nessan J Kerrigan.   

Abstract

The development of a BINAPHANE-catalyzed formal [2 + 2]-cycloaddition of disubstituted ketenes and inexpensive N-tosyl arylimines that provides access to a variety of highly substituted β-lactams (16 examples) is described. The BINAPHANE catalytic system displays moderate to excellent enantioselectivity (up to 98% ee) and high diastereoselectivity in most cases, favoring formation of the trans-diastereomer (13 examples with dr ≥ 90:10).

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Year:  2012        PMID: 22409456     DOI: 10.1021/ol3003783

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


  8 in total

1.  Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

Authors:  Shi Chen; Ahmad A Ibrahim; Nicholas J Peraino; Divya Nalla; Mukulesh Mondal; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-08-12       Impact factor: 4.354

2.  Alkaloid-Catalyzed Enantioselective [3 + 2] Cycloaddition of Ketenes and Azomethine Imines.

Authors:  Mukulesh Mondal; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005

Review 3.  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

4.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

5.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

6.  Enantioselective cis-β-lactam synthesis by intramolecular C-H functionalization from enoldiazoacetamides and derivative donor-acceptor cyclopropenes.

Authors:  Xinfang Xu; Yongming Deng; David N Yim; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Sci       Date:  2015-04-01       Impact factor: 9.825

7.  Lewis Base Catalyzed Synthesis of Sulfur Heterocycles via the C1-Pyridinium Enolate.

Authors:  Simon Cromwell; Randy Sutio; Changhe Zhang; Georgina K Such; David W Lupton
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-11       Impact factor: 16.823

Review 8.  Chiral phosphines in nucleophilic organocatalysis.

Authors:  Yumei Xiao; Zhanhu Sun; Hongchao Guo; Ohyun Kwon
Journal:  Beilstein J Org Chem       Date:  2014-09-04       Impact factor: 2.883

  8 in total

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