4.4 Article

Asymmetric cyclization-carbonylation of 2-alkyl-2-propargylcyclohexane-1,3-diones: facile access to optically active hydrindanes

Journal

TETRAHEDRON
Volume 64, Issue 2, Pages 319-327

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.10.106

Keywords

palladium; bisoxazoline; asymmetric; wacker-type cyclization; carbonylation; hydrindane

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Oxidative cyclization - carbonylation of 2-alkyl-2-propargylcyclohexane-1,3-diones mediated by Pd(TFA)(2)/2,2'-isopropylidenebis[(4R)4-(3,4-dimethoxyphenyl)-2-oxazoline] 28 afforded bicyclic-beta-alkoxyacrylates in 51 - 74% yields with 72 - 82% ee. The products containing quaternary carbon were converted to optically active hydrindanes 33. (c) 2007 Elsevier Ltd. All rights reserved.

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