Issue 20, 2003

Stereochemistry of intramolecular Diels–Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides

Abstract

This paper describes the stereoselective outcome of the intramolecular Diels–Alder furan (IMDAF) reaction of substituted (2S,3S)-ethanolamides 9–13, which were synthesised from a furyl substituted cyanohydrin. The latter was obtained from 2-furaldehyde with high enantioselectivity by an oxynitrilase catalysed addition of hydrogen cyanide. The stereochemistry of the IMDAF products was shown to be dependent on the size of the ethanolamide substituents R. Small substituents (H, Me, CN) gave exclusively exo-cycloaddition, whereas more bulky ones (Ph, Et) gave both exo- and endo-addition, the larger phenyl substituent giving a high endoexo-ratio.

Graphical abstract: Stereochemistry of intramolecular Diels–Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides

Supplementary files

Article information

Article type
Paper
Submitted
27 Jun 2003
Accepted
27 Aug 2003
First published
19 Sep 2003

Org. Biomol. Chem., 2003,1, 3592-3599

Stereochemistry of intramolecular Diels–Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides

R. A. Tromp, J. Brussee and A. van der Gen, Org. Biomol. Chem., 2003, 1, 3592 DOI: 10.1039/B307275D

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