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Flexible Synthesis of Enantiomerically Pure 2,8-Dialkyl-1,7-dioxaspiro[5.5]undecanes and 2,7-Dialkyl-1,6-dioxaspiro[4.5]decanes from Propargylic and Homopropargylic Alcohols

Schwartz, Brett; Hayes, Patricia Y; Kitching, William; De Voss, James Joseph


(Chemical Equation Presented) A new approach to enantiomerically pure 2,8-dialkyl-1,7-dioxaspiro[5.5]undecanes and 2,7-dialkyl-1,6-dioxaspiro[4.5] decanes is described and utilizes enantiomerically pure homopropargylic alcohols obtained from lithium acetylide opening of enantiomerically pure epoxides, which are, in turn, acquired by hydrolytic kinetic resolution of the corresponding racemic epoxides. Alkyne carboxylation and conversion to the Weinreb amide may be followed by triple-bond...[Show more]

CollectionsANU Research Publications
Date published: 2005
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/jo0477547


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