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2005
Terpenes
U 0200
01- 160
An Unusual Domino Retro-Ene—Conia Reaction: Regio- and Stereoselective
One-Carbon Ring Expansion of Fenchol Derivatives. — A novel, thermally promoted domino retro-ene-Conia rearrangement of 2-exo-substituted fenchol derivatives
affording optically active bicyclo[3.2.1.]octan-2-ones is described. Despite temperatures above 600°C, the fragmentation/recyclization process occurs with no loss of optical activity. In cases where the ring expanded products are sterically too congested
(cf. (XII)), unusual subsequent reactions, e.g. dealkylations or 1,3-C shifts, allow the
system to relax. — (RUEEDI*, G.; LAIKOV, D. N.; HANSEN, H.-J.; Helv. Chim.
Acta 87 (2004) 8, 1990-2021; Org.-Chem. Inst., Univ. Zuerich, CH-8057 Zuerich,
Switz.; Eng.) — Bartels
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