Literature DB >> 28474515

Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides.

Stephen W Laws1, Lucas C Moore1, Michael J Di Maso1, Q Nhu N Nguyen1, Dean J Tantillo1, Jared T Shaw1.   

Abstract

A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.

Entities:  

Year:  2017        PMID： 28474515      PMCID： PMC5576723          DOI： 10.1021/acs.orglett.7b00468

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


  22 in total

1.  Diastereoselective synthesis of gamma-lactams by a one-pot, four-component reaction.

Authors:  Jingqiang Wei; Jared T Shaw
Journal:  Org Lett       Date:  2007-08-31       Impact factor: 6.005

2.  Cyclic anhydrides in formal cycloadditions and multicomponent reactions.

Authors:  Marcos González-López; Jared T Shaw
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

3.  The condensation of succinic anhydride with benzylidinemethylamine. A stereoselective synthesis of trans- and cis-1-methyl-4-carbosy-5-phenyl-2-pyrrolidinone.

Authors:  N Castagnoli
Journal:  J Org Chem       Date:  1969-10       Impact factor: 4.354

4.  Stereocontrol in asymmetric γ-lactam syntheses from imines and cyanosuccinic anhydrides.

Authors:  Ommidala Pattawong; Darlene Q Tan; James C Fettinger; Jared T Shaw; Paul Ha-Yeon Cheong
Journal:  Org Lett       Date:  2013-09-26       Impact factor: 6.005

5.  The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands.

Authors:  Stefan Dahmen; Stefan Bräse
Journal:  J Am Chem Soc       Date:  2002-05-29       Impact factor: 15.419

6.  Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction.

Authors:  Ashkaan Younai; Gregory F Chin; Jared T Shaw
Journal:  J Org Chem       Date:  2010-11-09       Impact factor: 4.354

7.  Phase transfer catalyzed enantioselective Strecker reactions of alpha-amido sulfones with cyanohydrins.

Authors:  Raquel P Herrera; Valentina Sgarzani; Luca Bernardi; Francesco Fini; Daniel Pettersen; Alfredo Ricci
Journal:  J Org Chem       Date:  2006-12-22       Impact factor: 4.354

8.  Trans-stereoselectivity in the reaction between homophthalic anhydride and imines.

Authors:  Yosu Vara; Tamara Bello; Eneko Aldaba; Ana Arrieta; José L Pizarro; María I Arriortua; Xabier Lopez; Fernando P Cossío
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

9.  Synthesis of amides and lactams in supercritical carbon dioxide.

Authors:  Xiao Yin Mak; Rocco P Ciccolini; Julia M Robinson; Jefferson W Tester; Rick L Danheiser
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

10.  Asymmetric strecker reaction of aldimines using aqueous potassium cyanide by phase-transfer catalysis of chiral quaternary ammonium salts with a tetranaphthyl backbone.

Authors:  Takashi Ooi; Yukitaka Uematsu; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419
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  1 in total

1.  Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.

Authors:  Claire L Jarvis; Neyra M Jemal; Spencer Knapp; Daniel Seidel
Journal:  Org Biomol Chem       Date:  2018-06-13       Impact factor: 3.876
  1 in total

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