Literature DB >> 15453735

Catalytic asymmetric hydroxymethylation of silicon enolates using an aqueous solution of formaldehyde with a chiral scandium complex.

Shunpei Ishikawa1, Tomoaki Hamada, Kei Manabe, Shū Kobayashi.   

Abstract

Catalytic asymmetric hydroxymethylation of silicon enolates has been achieved. In this reaction, an aqueous solution of formaldehyde can be used to realize an easy and safe procedure, and high enantioselectivities have been obtained. This is the first example of catalytic asymmetric reactions in aqueous media with a chiral scandium complex.

Entities:  

Year:  2004        PMID： 15453735     DOI： 10.1021/ja047896i

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates.

Authors:  Xinfang Xu; Wen-Hao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-31       Impact factor: 15.336

2.  Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: synthesis of highly functionalized cyclopentanones.

Authors:  Phong Truong; Charles S Shanahan; Michael P Doyle
Journal:  Org Lett       Date:  2012-06-28       Impact factor: 6.005

3.  Structural Characterization of Methanol Substituted Lanthanum Halides.

Authors:  Timothy J Boyle; Leigh Anna M Ottley; Todd M Alam; Mark A Rodriguez; Pin Yang; Sarah K McIntyre
Journal:  Polyhedron       Date:  2010-05-10       Impact factor: 3.052

4.  Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Authors:  Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

5.  Synthetic and biosynthetic studies on FR900482 and mitomycin C: an efficient and stereoselective hydroxymethylation of an advanced benzazocane intermediate.

Authors:  Hidenori Namiki; Stephen Chamberland; Daniel A Gubler; Robert M Williams
Journal:  Org Lett       Date:  2007-11-30       Impact factor: 6.005

Review 6.  Synthesis and Application of the Transition Metal Complexes of α-Pyridinyl Alcohols, α-Bipyridinyl Alcohols, α,α'-Pyridinyl Diols and α,α'-Bipyridinyl Diols in Homogeneous Catalysis.

Authors:  Tegene Tole; Johannes Jordaan; Hermanus Vosloo
Journal:  Molecules       Date:  2018-04-12       Impact factor: 4.411

Review 7.  Mukaiyama Aldol Reactions in Aqueous Media.

Authors:  Taku Kitanosono; Shū Kobayashi
Journal:  Adv Synth Catal       Date:  2013-10-31       Impact factor: 5.837

8.  Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes.

Authors:  Robin Jastrzebski; Sandra Constant; Christopher S Lancefield; Nicholas J Westwood; Bert M Weckhuysen; Pieter C A Bruijnincx
Journal:  ChemSusChem       Date:  2016-07-21       Impact factor: 8.928
  8 in total

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