Prins-pinacol spiroannulations

DOI: 10.1016/S0040-4020(97)90401-4

Source and publish data:

Tetrahedron p. 8927 - 8940 (1997)

Update date:2022-07-29

Topics:

Authors:

Minor, Keith P.

Overman, Larry E.

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Article abstract of DOI:10.1016/S0040-4020(97)90401-4

Lewis acid-promoted cyclizations of methylenecyclohexane siloxy acetals 14, 15, and 21 afford spiro[4.5]decanones 22, 25, and 29 in good yield. In all cases, exclusive pinacol rearrangement of C-1 of the original three- carbon acetal side chain is observed suggesting that pinacol rearrangement of the intermediate 9-decalyl cation occurs more rapidly than conformational equilibration. This selectivity should allow Prins-pinacol spiroannulations to be employed in a predictable fashion to construct stereochemically complex spirocycles.

Full text of DOI:10.1016/S0040-4020(97)90401-4

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Product name:Silane, [[2-(3,3-dimethoxypropyl)-1-cyclohexen-1-yl]oxy]trimethyl-

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