Literature DB >> 17760458

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

Jingqiang Wei1, Jared T Shaw.   

Abstract

A new one-pot, four-component reaction (4CR) between amines, maleic anhydrides, aldehydes, and thiols has been discovered to form tetra- and pentasubstituted gamma-lactams with high diastereoselectivity. Each component is independently variable and employed in equivalent stoichiometry, producing only water as a byproduct.

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Year:  2007        PMID： 17760458     DOI： 10.1021/ol701911u

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


  13 in total

1.  Ammonia synthons for the multicomponent assembly of complex gamma-lactams.

Authors:  Darlene Q Tan; Kevin S Martin; James C Fettinger; Jared T Shaw
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-02       Impact factor: 11.205

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

Authors:  Stephen W Laws; Lucas C Moore; Michael J Di Maso; Q Nhu N Nguyen; Dean J Tantillo; Jared T Shaw
Journal:  Org Lett       Date:  2017-05-05       Impact factor: 6.005

3.  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

4.  Synthesis of a γ-lactam library via formal cycloaddition of imines and substituted succinic anhydrides.

Authors:  Darlene Q Tan; Amy L Atherton; Austin J Smith; Cristian Soldi; Katherine A Hurley; James C Fettinger; Jared T Shaw
Journal:  ACS Comb Sci       Date:  2012-02-10       Impact factor: 3.784

5.  Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for the Cadogan and Davis-Beirut Reactions.

Authors:  Jie S Zhu; Clarabella J Li; Ka Yi Tsui; Niklas Kraemer; Jung-Ho Son; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
Journal:  J Am Chem Soc       Date:  2019-04-04       Impact factor: 15.419

6.  The p53-MDM2/MDMX axis - A chemotype perspective.

Authors:  Kareem Khoury; Grzegorz M Popowicz; Tad A Holak; Alexander Dömling
Journal:  Medchemcomm       Date:  2011       Impact factor: 3.597

7.  Synthesis of a library of "lead-like" γ-lactams by a one pot, four-component reaction.

Authors:  Kevin S Martin; Michael J Di Maso; James C Fettinger; Jared T Shaw
Journal:  ACS Comb Sci       Date:  2013-06-12       Impact factor: 3.784

8.  Efficient synthesis of gamma-lactams by a tandem reductive amination/lactamization sequence.

Authors:  Julica Nöth; Kevin J Frankowski; Benjamin Neuenswander; Jeffrey Aubé; Oliver Reiser
Journal:  J Comb Chem       Date:  2008-03-14

9.  Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.

Authors:  Christopher G Evans; Jason E Gestwicki
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

Review 10.  New one-pot methodologies for the modification or synthesis of alkaloid scaffolds.

Authors:  Amir E Wahba; Mark T Hamann
Journal:  Mar Drugs       Date:  2010-08-24       Impact factor: 5.118
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