Literature DB >> 16706545

Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group.

Patrick Aschwanden1, Corey R J Stephenson, Erick M Carreira.   

Abstract

[reaction: see text] We report a highly enantioselective, catalytic three-component coupling of aldehydes, alkynes, and 4-piperidone hydrochloride hydrate to afford the corresponding tertiary propargylamines in useful yields. The selective cleavage of the piperidone protecting group using either ammonia/EtOH or a polymer-supported scavenger amine furnishes primary propargylamines.

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Year:  2006        PMID: 16706545     DOI: 10.1021/ol060876w

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


  6 in total

1.  Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors:  Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
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2.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

3.  Enhancing Potency and Selectivity of a DC-SIGN Glycomimetic Ligand by Fragment-Based Design: Structural Basis.

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Journal:  Chemistry       Date:  2019-10-18       Impact factor: 5.236

4.  Pyrinap ligands for enantioselective syntheses of amines.

Authors:  Qi Liu; Haibo Xu; Yuling Li; Yuan Yao; Xue Zhang; Yinlong Guo; Shengming Ma
Journal:  Nat Commun       Date:  2021-01-04       Impact factor: 14.919

5.  Platinum-(phosphinito-phosphinous acid) complexes as bi-talented catalysts for oxidative fragmentation of piperidinols: an entry to primary amines.

Authors:  Romain Membrat; Alexandre Vasseur; Delphine Moraleda; Sabine Michaud-Chevallier; Alexandre Martinez; Laurent Giordano; Didier Nuel
Journal:  RSC Adv       Date:  2019-11-20       Impact factor: 3.361

6.  Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow.

Authors:  Hyowon Seo; Matthew H Katcher; Timothy F Jamison
Journal:  Nat Chem       Date:  2016-12-26       Impact factor: 24.427

  6 in total

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