Literature DB >> 20552963

General access to chiral N-alkyl terminal aziridines via organocatalysis.

Olugbeminiyi O Fadeyi1, Michael L Schulte, Craig W Lindsley.   

Abstract

A three step, one-pot protocol involving enantioselective alpha-chlorination of aldehydes, subsequent reductive amination with a primary amine, and S(N)2 displacement to afford chiral N-alkyl terminal aziridines in 40-65% yield (74-87%/step) and, in most cases, >90% ee is reported.

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Year:  2010        PMID: 20552963     DOI: 10.1021/ol101276x

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


  6 in total

1.  A general, enantioselective synthesis of protected morpholines and piperazines.

Authors:  Matthew C O'Reilly; Craig W Lindsley
Journal:  Org Lett       Date:  2012-05-22       Impact factor: 6.005

2.  CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.

Authors:  Haoxuan Wang; Jeffrey C Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-15       Impact factor: 15.419

3.  Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N'-protected piperazines via organocatalysis.

Authors:  Matthew C O'Reilly; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2011-12-29       Impact factor: 2.415

4.  A general, enantioselective synthesis of β- and γ-fluoroamines.

Authors:  Matthew C O'Reilly; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-07-10       Impact factor: 2.415

5.  A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis.

Authors:  Timothy J Senter; Matthew C O'Reilly; Katherine M Chong; Gary A Sulikowski; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2015-03-04       Impact factor: 2.415

Review 6.  Facile and Green Synthesis of Saturated Cyclic Amines.

Authors:  Arruje Hameed; Sadia Javed; Razia Noreen; Tayyaba Huma; Sarosh Iqbal; Huma Umbreen; Tahsin Gulzar; Tahir Farooq
Journal:  Molecules       Date:  2017-10-12       Impact factor: 4.411

  6 in total

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