Ruthenium-catalyzed Asymmetric Dehydrative Allylic Cyclization of Chalcogen 5-Membered Heteroaromatics
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The asymmetric dehydrative intramolecular allylation reactions of furan and thiophene were performed using a cationic cyclopentadienyl-ruthenium (CpRu) complex of a chiral pyridine carboxylic acid, namely Cl-Naph-PyCOOH. Both furan and thiophene tethered with an allylic alcohol gave the corresponding bicyclic compounds in high yields and enantioselectivities using 0.1–5 mol% of catalyst. The reaction was found to proceed via a similar enantioface selection method mechanism to that previously reported by our group, which involved halogen and hydrogen bond formation, in addition to the generation of an intermediate σ-allyl complex.
1982 ◽
Vol 104
(2)
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pp. 619-621
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2004 ◽
Vol 108
(19)
◽
pp. 4357-4364
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