Aqueous cycloaddition using glyco-organic substrates. Facial stereoselectivity in Diels–Alder reactions of a chiral diene derived fromD-glyceraldehyde
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 3011-3015
- https://doi.org/10.1039/p19900003011
Abstract
The preparation of a new chiral, water-soluble E-diene, which could be considered as the simplest diene obtainable from the simplest sugar, is described, along with its use in cycloaddition with acrylaldehyde. Water, as the solvent, enhanced the rate of the Diels–Alder reaction, promoted complete regio- and endo-selectivity, and improved a like(anti) facial selectivity, compared with the results obtained with organic solvents.This publication has 27 references indexed in Scilit:
- Stereochemical variations in aqueous cycloadditions using glyco-organic substrates as a consequence of chemical manipulations on the sugar moiety.Tetrahedron, 1989
- Diels-Alder reactions of acyclic chiral alkoxy dienes: Oxygen versus sulfur as an allylic directing groupTetrahedron Letters, 1989
- Formation of chiral alkoxy dienes in Wittig/Michael reactions of 2,3,5-tri-O-benzyl-D-arabinoseThe Journal of Organic Chemistry, 1987
- .pi.-Facial selection in intermolecular Diels-Alder reactions: total syntheses of (+)-actinobolin and (+)-5,6,10-triepiactinobolinJournal of the American Chemical Society, 1987
- Aqueous cycloadditions using glyco-organic substrates. 1. Stereochemical course of the reactionThe Journal of Organic Chemistry, 1987
- Modeling chemical reactivity. 5. Facial selectivity in Diels-Alder cycloadditionsJournal of the American Chemical Society, 1987
- Direct .beta.-lithiation of 2-alkoxy dienes: use in an asymmetric Diels-Alder reactionThe Journal of Organic Chemistry, 1986
- An examination of π-facial selectivity in the diels-alder reaction of a chiral diene - a synthesis of (+)-5,6,10-tri-(EPI)-Actinobolin.Tetrahedron Letters, 1986
- The face selectivity directed by an allylic group of a diene in the diels-alder reaction is reversed from that of a dienophileTetrahedron Letters, 1985
- Stereoselective synthesis and Diels-Alder reactions of bis-Ether 1,3 Dienes. A further test for cooperativity during cycloaddition reactions.Tetrahedron Letters, 1984