Literature DB >> 27498770

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

Mukulesh Mondal1, Kraig A Wheeler2, Nessan J Kerrigan1.   

Abstract

A new asymmetric synthesis of bicyclic pyrazolidinones through an alkaloid-catalyzed formal [3 + 2] cycloaddition of in situ generated ketenes and azomethine imines is described. The products were formed in good to excellent yields (52-99% for 17 examples), with good to excellent diastereoselectivity (dr 5:1 to 27:1 for 11 examples), and with excellent enantioselectivity in all cases (≥96% ee). This method represents the first unambiguous example of an enantioselective reaction between ketenes and a 1,3-dipole.

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Year:  2016        PMID： 27498770      PMCID： PMC5012990          DOI： 10.1021/acs.orglett.6b02038

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


  15 in total

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

Authors:  Shi Chen; Eric C Salo; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

2.  Catalytic asymmetric heterodimerization of ketenes.

Authors:  Ahmad A Ibrahim; Divya Nalla; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Am Chem Soc       Date:  2012-02-03       Impact factor: 15.419

3.  Formal [3+2] cycloaddition of ketenes and oxaziridines catalyzed by chiral Lewis bases: enantioselective synthesis of oxazolin-4-ones.

Authors:  Pan-Lin Shao; Xiang-Yu Chen; Song Ye
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

4.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

5.  Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes.

Authors:  Varinder K Aggarwal; Jeremy N Harvey; Jeffery Richardson
Journal:  J Am Chem Soc       Date:  2002-05-22       Impact factor: 15.419

6.  The development of the first catalyzed reaction of ketenes and imines: catalytic, asymmetric synthesis of beta-lactams.

Authors:  Andrew E Taggi; Ahmed M Hafez; Harald Wack; Brandon Young; Dana Ferraris; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

7.  Phosphine-catalyzed asymmetric synthesis of β-lactones from disubstituted ketenes and aldehydes.

Authors:  Shi Chen; Mukulesh Mondal; Ahmad A Ibrahim; Kraig A Wheeler; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2014-05-08       Impact factor: 4.354

8.  Organocatalysed multicomponent synthesis of pyrazolidinones: Meldrum's acid approach.

Authors:  Etienne Pair; Christophe Berini; Romain Noël; Morgane Sanselme; Vincent Levacher; Jean-François Brière
Journal:  Chem Commun (Camb)       Date:  2014-09-14       Impact factor: 6.222

9.  A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.

Authors:  Ryo Shintani; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

10.  Catalytic, asymmetric preparation of ketene dimers from acid chlorides.

Authors:  Michael A Calter; Robert K Orr; Wei Song
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  2 in total

Review 1.  Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines.

Authors:  Franc Požgan; Hamad Al Mamari; Uroš Grošelj; Jurij Svete; Bogdan Štefane
Journal:  Molecules       Date:  2017-12-21       Impact factor: 4.411

2.  Asymmetric Synthesis of Bicyclic Pyrazolidinones through Alkaloid-Catalyzed [3+2]-Cycloadditions of Ketenes and Azomethine Imines.

Authors:  Mukulesh Mondal; Shubhanjan Mitra; Dylan J Twardy; Manashi Panda; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Chemistry       Date:  2022-03-14       Impact factor: 5.020
  2 in total

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