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Short Communication
Enantioselective Synthesis and Circular Dichroism of Endocyclic Allenes
Article first published online: 16 SEP 2004
DOI: 10.1002/ejoc.200400408
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Zelder, C. and Krause, N. (2004), Enantioselective Synthesis and Circular Dichroism of Endocyclic Allenes. European Journal of Organic Chemistry, 2004: 3968–3971. doi: 10.1002/ejoc.200400408
Publication History
- Issue published online: 16 SEP 2004
- Article first published online: 16 SEP 2004
- Manuscript Received: 9 JUN 2004
- Abstract
- Article
- References
- Cited By
Keywords:
- Allenes;
- Chirality;
- Circular dichroism;
- Kinetic resolution
Graphical Abstract
Abstract
The novel, enantiomerically enriched nine- and ten-membered cyclic allenes (+)-5a−c and (−)-6a−c were synthesized by lipase-catalyzed kinetic resolution of propargylic acetates 1/2 and subsequent anti-stereoselective SN2′-substitution with magnesium cuprates. The CD spectra of these allenes exhibit distinct features that are a function of the ring size and the alkyl substituent at the allene moiety. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)