Stereoselective Synthesis of Tetrahydropyran-4-ones from Dioxinones Catalyzed by Scandium(III) Triflate
- 11 February 2005
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (6) , 1113-1116
- https://doi.org/10.1021/ol050093v
Abstract
A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and β-hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in situ addition fragments the dioxinone rings and delivers the 3-carboxy-substituted tetrahydropyran-4-ones in good yields with high levels of diastereoselectivity.Keywords
This publication has 7 references indexed in Scilit:
- Axial-Selective Prins Cyclizations by Solvolysis of α-Bromo EthersJournal of the American Chemical Society, 2004
- A Planning Strategy for Diversity‐Oriented SynthesisAngewandte Chemie International Edition in English, 2003
- New Efficient Iterative Approaches to Polycyclic EthersChemistry – A European Journal, 2002
- Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) CatalystsAngewandte Chemie International Edition in English, 1999
- Stereocontrolled Synthesis of Trisubstituted TetrahydropyransJournal of the American Chemical Society, 1999
- Catalytic, Enantioselective Dienolate Additions to Aldehydes: Preparation of Optically Active Acetoacetate Aldol AdductsJournal of the American Chemical Society, 1995
- Acetoacetylation with 2,2,6-trimethyl-4H-1,3-dioxin-4-one: a convenient alternative to diketeneThe Journal of Organic Chemistry, 1985