Regioselective and stereoselective reductive cleavage of 1,7-dioxaspiro[5.5]undecane alcohols

DOI: 10.1016/0040-4039(96)01196-3

Source and publish data:

Tetrahedron Letters p. 5649 - 5652 (1996)

Update date:2022-08-03

Topics:

Authors:

Crimmins, Michael T.

Rafferty, Stephen W.

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Article abstract of DOI:10.1016/0040-4039(96)01196-3

Lewis acid-promoted triethylsilane reduction of 6,6-spiroketal alcohols produces cis-2,6-disubstituted tetrahydropyrans with excellent regioselectivity and stereocontrol. An appended alcohol allows bidentate coordination of the Lewis acid to selectively activate one C-O bond of the anomeric center toward reductive cleavage.

Full text of DOI:10.1016/0040-4039(96)01196-3

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