Literature DB >> 27218461

[3 + 2]-Cycloadditions of Azomethine Imines and Ynolates.

Sarah E Winterton1, Joseph M Ready1.   

Abstract

A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diastereoselectivity and stereospecificity allow access to optically active products.

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Year:  2016        PMID： 27218461      PMCID： PMC4961353          DOI： 10.1021/acs.orglett.6b01104

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


  20 in total

1.  Asymmetric 1,3-Dipolar Cycloaddition Reactions.

Authors:  Kurt V. Gothelf; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Reactions of (trialkylsilyl)vinylketenes with lithium ynolates: a new benzannulation strategy.

Authors:  Wesley F Austin; Yongjun Zhang; Rick L Danheiser
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

3.  Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates.

Authors:  Mitsuru Shindo; Yutaka Yoshimura; Maiko Hayashi; Hiroe Soejima; Takashi Yoshikawa; Kenji Matsumoto; Kozo Shishido
Journal:  Org Lett       Date:  2007-04-17       Impact factor: 6.005

4.  Ynolate chemistry. Reaction of a silylynolate with aziridines leading to gamma-lactams.

Authors:  K Iwamoto; M Kojima; N Chatani; S Murai
Journal:  J Org Chem       Date:  2001-01-12       Impact factor: 4.354

5.  Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with alpha,beta-unsaturated aldehydes.

Authors:  Takuya Hashimoto; Yuko Maeda; Masato Omote; Hiroki Nakatsu; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

6.  Anionic inverse electron-demand 1,3-dipolar cycloaddition of nitrones with ynolates. Facile stereoselective synthesis of 5-isoxazolidinones leading to beta-amino acids.

Authors:  Mitsuru Shindo; Kotaro Itoh; Chinatsu Tsuchiya; Kozo Shishido
Journal:  Org Lett       Date:  2002-09-05       Impact factor: 6.005

7.  Silver-catalyzed [2 + 2] cycloadditions of siloxy alkynes.

Authors:  Randy F Sweis; Michael P Schramm; Sergey A Kozmin
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

8.  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

9.  Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes.

Authors:  Takaki Imaizumi; Yasuhiro Yamashita; Shū Kobayashi
Journal:  J Am Chem Soc       Date:  2012-12-04       Impact factor: 15.419

10.  Copper(I) zeolites as heterogeneous and ligand-free catalysts: [3+2] cycloaddition of azomethine imines.

Authors:  Murielle Keller; Abdelkarim Sani Souna Sido; Patrick Pale; Jean Sommer
Journal:  Chemistry       Date:  2009       Impact factor: 5.236
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  3 in total

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

Authors:  Mukulesh Mondal; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005

2.  Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol.

Authors:  Xinxin Dang; Yu He; Yingtian Liu; Xuehong Chen; Jun-Long Li; Xian-Li Zhou; Hezhong Jiang; Jiahong Li
Journal:  RSC Adv       Date:  2018-08-24       Impact factor: 4.036

3.  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
  3 in total

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