Literature DB >> 23670946

Rh-catalyzed direct enantioselective alkynylation of α-ketiminoesters.

Kazuhiro Morisaki1, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Takashi Ohshima.   

Abstract

A green way to amino acids: α-Tetrasubstituted α-amino acid derivatives are formed in high yield and enantioselectivity by using a Rh-catalyzed enantioselective alkynylation of α-ketiminoesters. This reaction, which involves a proton transfer and can be conducted at room temperature, has high substrate scope (see scheme; Cbz = benzyloxycarbonyl, Fmoc = 9-fluorenylmethyloxycarbonyl).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID: 23670946     DOI: 10.1002/chem.201301237

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  A Broad Substrate Scope of Aza-Friedel-Crafts Alkylation for the Synthesis of Quaternary α-Amino Esters.

Authors:  Guangkuan Zhao; Shyam S Samanta; Jessica Michieletto; Stéphane P Roche
Journal:  Org Lett       Date:  2020-07-10       Impact factor: 6.005

3.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

4.  Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles.

Authors:  Ziyi Li; Li Wang; Yunqi Huang; Haibo Mei; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok; Jianlin Han
Journal:  Beilstein J Org Chem       Date:  2020-10-29       Impact factor: 2.883

5.  Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.

Authors:  Camilla Pfeffer; Patrick Probst; Nick Wannenmacher; Wolfgang Frey; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-19       Impact factor: 16.823

6.  Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement.

Authors:  Xi-Shang Sun; Xing-Heng Wang; Hai-Yan Tao; Liang Wei; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2020-09-17       Impact factor: 9.825

7.  Pd-Catalyzed Allylation of Imines to Access α-CF3-Substituted α-Amino Acid Derivatives.

Authors:  Michael Winter; Hyunwoo Kim; Mario Waser
Journal:  European J Org Chem       Date:  2019-10-09
  7 in total

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