Literature DB >> 12203626

Catalytic Enantioselective Addition of Nitro Compounds to Imines-A Simple Approach for the Synthesis of Optically Active β-Nitro-α-Amino Esters.

N Nishiwaki1, K Rahbek Knudsen, K V Gothelf, K A Jørgensen.   

Abstract

The catalytic and asymmetric nitro-Mannich reaction of nitro compounds to α-imino esters catalyzed by chiral bisoxazoline-copper complexes [Eq. (1); Pg = protecting group] gave β-nitro-α-amino esters with excellent diastereo- and enantioselectivities. The reactions can be performed under ambient conditions.
Copyright © 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Lewis acids; amino acids; asymmetric catalysis; imines; nitro compounds

Year:  2001        PMID： 12203626     DOI： 10.1002/1521-3773(20010817)40:16<2992::AID-ANIE2992>3.0.CO;2-3

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  Catalytic, Enantioselective Synthesis of Stilbene cis-Diamines: A Concise Preparation of (-)-Nutlin-3, a Potent p53/MDM2 Inhibitor.

Authors:  Tyler A Davis; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2011-03-25       Impact factor: 9.825

2.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

3.  A Novel Bis-Thiourea Organocatalyst for the Asymmetric Aza-Henry Reaction.

Authors:  Constantinos Rampalakos; William D Wulff
Journal:  Adv Synth Catal       Date:  2008-08-04       Impact factor: 5.837

4.  Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives.

Authors:  Jian-Xin Ji; Jing Wu; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2005-08-01       Impact factor: 11.205

5.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

6.  Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.

Authors:  Sergey V Tsukanov; Martin D Johnson; Scott A May; Morgan Rosemeyer; Michael A Watkins; Stanley P Kolis; Matthew H Yates; Jeffrey N Johnston
Journal:  Org Process Res Dev       Date:  2016-02-01       Impact factor: 3.317

7.  Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.

Authors:  Brandon A Vara; Anand Mayasundari; John C Tellis; Michael W Danneman; Vanessa Arredondo; Tyler A Davis; Jaeki Min; Kristin Finch; R Kiplin Guy; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354

8.  Preparation of H,(4) PyrrolidineQuin-BAM (PBAM).

Authors:  Tyler A Davis; Mark C Dobish; Kenneth E Schwieter; Aspen C Chun; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2012-02-22

9.  Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe.

Authors:  Motoyuki Isoda; Kazuyuki Sato; Yurika Kunugi; Satsuki Tokonishi; Atsushi Tarui; Masaaki Omote; Hideki Minami; Akira Ando
Journal:  Beilstein J Org Chem       Date:  2016-07-27       Impact factor: 2.883

10.  Catalytic asymmetric nitro-Mannich reactions with a Yb/K heterobimetallic catalyst.

Authors:  Tatsuya Nitabaru; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Molecules       Date:  2010-03-04       Impact factor: 4.411
  10 in total

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