Literature DB >> 23308040

Stereochemical Studies of Ag-Catalyzed Hosomi-Sakurai Reaction Using Chiral Silanes.

Manabu Wadamoto1, Marina Naodovic, Hisashi Yamamoto.   

Abstract

Stereochemical aspect of asymmetric Ag-catalyzed Hosomi-Sakurai reaction with ketones has been investigated. Several allyltrimethoxysilanes have been synthesized and used for the asymmetric reaction. Remarkably, among several possible diastereomers only two are generated with high levels of diastereo- and enantioselectivities. Based on the observations for different allyltimethoxysilanes, we hypothesize formation of a single allylsilver species which undergoes addition to the ketone.

Entities:  

Year:  2009        PMID: 23308040      PMCID: PMC3539815          DOI: 10.1002/ejoc.200900670

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


  4 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 2.  Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool.

Authors:  Barry M Trost
Journal:  Chem Pharm Bull (Tokyo)       Date:  2002-01       Impact factor: 1.645

3.  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

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

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

1.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

2.  Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones.

Authors:  Jian-Jun Feng; Yan Xu; Martin Oestreich
Journal:  Chem Sci       Date:  2019-08-20       Impact factor: 9.825

  2 in total

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