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Literature DB >> 15954759

Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications.

Barry M Trost¹, Seunghoon Shin, Joseph A Sclafani.

Abstract

A direct catalytic asymmetric aldol reaction of methyl vinyl ketone is described using our dinuclear zinc catalyst. The obtained aldol adduct functions as a bifunctional building block by utilization of the vinyl functionality. For example, convergent fragment coupling methods have been demonstrated via highly diastereoselective cycloaddition of nitrile oxide after reduction into 1,3-diol or via cross-metathesis reaction.

Entities: Chemical

Mesh：

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Year: 2005 PMID： 15954759 PMCID： PMC2535804 DOI： 10.1021/ja051526s

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

16 in total

1. Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts.

Authors: B M Trost; E R Silcoff; H Ito
Journal: Org Lett Date: 2001-08-09 Impact factor: 6.005

2. Recent developments in olefin cross-metathesis.

Authors: Stephen J Connon; Siegfried Blechert
Journal: Angew Chem Int Ed Engl Date: 2003-04-29 Impact factor: 15.336

3. Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine.

Authors: Barry M Trost; Vince S C Yeh; Hisanako Ito; Nadine Bremeyer
Journal: Org Lett Date: 2002-08-08 Impact factor: 6.005

10. Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks.

Authors: Barry M Trost; Sushant Malhotra; Takashi Mino; Naomi S Rajapaksa
Journal: Chemistry Date: 2008 Impact factor: 5.236

Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications.

1. Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts.

2. Recent developments in olefin cross-metathesis.

3. Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine.

4. A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction.

5. Synthesis and evaluation of lasonolide A analogues.

6. Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction.

7. A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones.

8. A general model for selectivity in olefin cross metathesis.

9. Stereocontrolled synthesis of (+)-boronolide.

10. A direct catalytic asymmetric mannich-type reaction to syn-amino alcohols.

Review 1. The direct catalytic asymmetric aldol reaction.

2. Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

3. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

4. Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D.

5. Atom-economic and stereoselective syntheses of the ring a and B subunits of the bryostatins.

6. Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

7. Total synthesis and stereochemical assignment of (-)-ushikulide A.

8. Broad Spectrum Enolate Equivalent for Catalytic Chemo-, Diastereo-, and Enantioselective Addition to N-Boc Imines.

9. Catalytic Asymmetric Mannich Reactions with Fluorinated Aromatic Ketones: Efficient Access to Chiral β-Fluoroamines.

10. Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks.