The synthesis of a new enantiomerically pure diene, (S)-(+)-1 is reported. The absolute configuration of 1 was determined by non-empirical analysis of its CD spectrum. The synthesis and resolution of the racemic β-diketone 4 into its constituent enantiomers by the SAMP-hydrazone method is described. The enantiopure β-diketone (S)-(+)-4 was then converted to diene (S)-(+)-1 by a two-stage reaction sequence. Structural analysis of the products by 1H and 13C NMR spectroscopy is also presented.

Synthesis and Absolute Configuration of a New Chiral [2.2]Paracyclophane-based Diene

ROSINI, Carlo;SUPERCHI, Stefano
2002

Abstract

The synthesis of a new enantiomerically pure diene, (S)-(+)-1 is reported. The absolute configuration of 1 was determined by non-empirical analysis of its CD spectrum. The synthesis and resolution of the racemic β-diketone 4 into its constituent enantiomers by the SAMP-hydrazone method is described. The enantiopure β-diketone (S)-(+)-4 was then converted to diene (S)-(+)-1 by a two-stage reaction sequence. Structural analysis of the products by 1H and 13C NMR spectroscopy is also presented.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11563/15141
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