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200517.fm Page 36 Friday, March 18, 2005 2:52 PM
2005
Enantioselective syntheses
O 0031
Catalytic Desymmetrizing Intramolecular Heck Reaction: Evidence for an
Hydroxy-Directed Migratory Insertion. — The palladium-catalyzed
17- 036 Unusual
intramolecular Heck reaction of bis(cinnamyl)arylethanol derivative (I) is smoothly
achieved in the presence of axially chiral diphosphine ligands to give enantioenriched
hydroxytetrahydronaphthalene derivative (II) in good yield and stereoselectivity. The
free hydroxy group is shown to play a crucial role in directing the catalyst. —
(OESTREICH*, M.; SEMPERE-CULLER, F.; MACHOTTA, A. B.; Angew. Chem.,
Int. Ed. 44 (2005) 1, 149-152; Inst. Org. Chem. Biochem., Albert-Ludwigs-Univ.,
D-79104 Freiburg/Br., Germany; Eng.) — Mischke
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