H. Brunner et A. Reimer, ENANTIOSELECTIVE CATALYSIS .112. NEW CHIRAL TERTIARY ALCOHOLS ON THE BASIS OF DELTACYCLANES AS PRECURSORS FOR HYDROPEROXIDES, Bulletin des Societes chimiques belges, 106(5), 1997, pp. 267-272
Norbornadiene was reacted with 2-methyl-3-butin-2-ol 1 in an enantiose
lective homo Diels-Alder reaction to yield the deltacyclene 2 with 92%
ee. 2 was hydrogenated stereoselectively to give the enantiomerically
pure, deltacyclane-based tertiary alcohol 3, a candidate for conversi
on into an optically active hydroperoxide for enantioselective oxidati
on reactions.