Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Acyclic 2‐Substituted‐1,3‐Propanediols: A Powerful Entry into Chiral Building Blocks
- 25 August 2008
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 14 (25) , 7648-7657
- https://doi.org/10.1002/chem.200800623
Abstract
The asymmetric acylation of meso‐2‐substituted‐1,3‐propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2‐alkyl‐ and 2‐aryl‐1,3‐propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.Keywords
This publication has 62 references indexed in Scilit:
- α‐Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of DiscodermolideAngewandte Chemie International Edition in English, 2007
- α‐Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of DiscodermolideAngewandte Chemie, 2007
- Total Synthesis of Jerangolid DJournal of the American Chemical Society, 2007
- Synthetic Stitching with Silicon: Geminal Alkylation−Hydroxylation of Alkynyl Carbonyl CompoundsJournal of the American Chemical Society, 2004
- Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted ShrimpHelvetica Chimica Acta, 2003
- A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) ReactionAngewandte Chemie, 2002
- Enzymatic Desymmetrization of Prochiral 2-Substituted-1,3-propanediols: A Practical Chemoenzymatic Synthesis of a Key Precursor of SCH51048, a Broad-Spectrum Orally Active Antifungal AgentThe Journal of Organic Chemistry, 1997
- Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical CyclizationThe Journal of Organic Chemistry, 1994
- Enzymatic Preparation of (R)-3-Hydroxy-2-Methylpropyl Butyrate by Asymmetric HydrolysisBiocatalysis, 1990
- Enantioselective synthesis of useful chiral precursors, unsymmetrical propane-1,3-diol derivatives, from malonic acidJournal of the Chemical Society, Chemical Communications, 1987