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:
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