Literature DB >> 20011620

Enantioselective Ag-Catalyzed Allylation of Aldimines.

Marina Naodovic1, Manabu Wadamoto, Hisashi Yamamoto.   

Abstract

A highly enantioselective synthesis of homoallylic amines, using allyltrimethoxysilane under Ag(I) catalytic conditions, has been developed. Among the chiral ligands investigated, a remarkable difference in the resulting Ag(I) complexes was observed. Under mild conditions and low catalyst loadings, homoallylamines were produced in high ee values (up to 80%) and good yields. The methodology can be further extended to a diastere- and enantioselective crotylation of aldimines.

Entities:  

Year:  2009        PMID： 20011620      PMCID： PMC2790292          DOI： 10.1002/ejoc.200900669

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  6 in total

1.  Catalytic enantioselective addition to imines.

Authors:  S Kobayashi; H Ishitani
Journal:  Chem Rev       Date:  1999-05-12       Impact factor: 60.622

2.  Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity.

Authors:  Robert Bloch
Journal:  Chem Rev       Date:  1998-06-18       Impact factor: 60.622

Review 3.  Asymmetric silver-catalyzed reactions.

Authors:  Marina Naodovic; Hisashi Yamamoto
Journal:  Chem Rev       Date:  2008-07-19       Impact factor: 60.622

4.  Silver-catalyzed asymmetric Sakurai-Hosomi allylation of ketones.

Authors:  Manabu Wadamoto; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

5.  Enantioselective O- and N-nitroso aldol synthesis of tin enolates. Isolation of three BINAP-silver complexes and their role in regio- and enantioselectivity.

Authors:  Norie Momiyama; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

6.  Silver-catalyzed asymmetric allylation: allyltrimethoxysilane as a remarkable reagent.

Authors:  Hisashi Yamamoto; Manabu Wadamoto
Journal:  Chem Asian J       Date:  2007-06-04
  6 in total
  4 in total

1.  Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.

Authors:  Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

2.  Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Authors:  Farid W van der Mei; Hiroshi Miyamoto; Daniel L Silverio; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-09       Impact factor: 15.336

3.  Simple organic molecules as catalysts for enantioselective synthesis of amines and alcohols.

Authors:  Daniel L Silverio; Sebastian Torker; Tatiana Pilyugina; Erika M Vieira; Marc L Snapper; Fredrik Haeffner; Amir H Hoveyda
Journal:  Nature       Date:  2013-02-14       Impact factor: 49.962

4.  An efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst.

Authors:  Hao Wu; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.