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Abstract
The preparation of 7- anti-(3-methyl-3-butenyl)norbornene 11 is described. This meso-symmetrical diene underwent ring-opening/ring-closing olefin metathesis catalyzed by bis(cyclopentadienyl)titanacyclobutane 4 to give (1R ∗, 6R ∗, 7S ∗) -7-ethenyl-3-methylbicyclo[4.3.0]non-2-ene as a single diastereomer. The less-substituted 7- anti-(3-butenyl)norbornene 1 did not react selectively at the norbornene double bond. Related 7-ester-substituted norbornenes underwent stoichiometric ring-opening/ring-closing olefin metathesis to give single diastereomers of bicyclic ketones after acidic work-up. Attempts to form a chiral Tebbe-type complex from ansa-{2,2′-bis[8-(bicyclo[4.3.0]-nona-1(6),7-dienyl)]-1,1′-binaphthyl}titanium dichloride 18 or a reactive chiral titanium carbene intermediate from its dimethyl derivative 20 were unsuccessful.
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