Intramolecular cyclization via iron tricarbonyl mediated coupling between cyclohexadienes and pendant olefins (or dienes)

ORGN 10

Anthony J. Pearson and Xiaolong Wang. Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, OH 44106

Intramolecular double cyclization between a cyclohexadiene-Fe(CO)3 complex and a pendant diene yielded a single tricyclic diastereomer under thermal conditions (JACS 2003, 125, 638, Eq. 1). Interestingly, when same substrates were subjected to cylization induced by trimethylamine N-oxide, an eight-membered ring was formed (Eq. 2), which will be discussed in detail along with related bicyclization reactions (Eq. 3).

Asymmetric Reactions and Syntheses 8:00 AM-12:00 PM, Sunday, September 7, 2003 Sheraton New York -- Imperial Ballroom A, Oral Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003