title: Lewis Acid Catalyzed Selective Reactions of Donor-Acceptor Cyclopropanes with 2-Naphthols.
abstract: Lewis acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with 2-naphthols is reported. The reaction exhibits tunable selectivity depending on the nature of Lewis acid employed and proceed as a dearomatization/rearomatization sequence. With Bi(OTf)3 as the Lewis acid, a highly selective dehydrative [3+2] cyclopentannulation takes place leading to the formation of naphthalene-fused cyclopentanes. Interestingly, engaging Sc(OTf)3 as the Lewis acid, a Friedel-Crafts-type addition of 2-naphthols to cyclopropanes takes place, thus affording functionalized 2-naphthols. Both reactions furnished the target products in high regioselectivity and moderate to high yields.
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-, 411008, India.|Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110020, India.
authors.forename: Trinadh
authors.initials: T
authors.lastname: Kaicharla
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-, 411008, India.|Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110020, India.
authors.forename: Tony
authors.initials: T
authors.lastname: Roy
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-, 411008, India.|Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110020, India.
authors.forename: Manikandan
authors.initials: M
authors.lastname: Thangaraj
authors.affiliation: Centre for Materials Characterization, CSIR-National Chemical Laboratory, Pune-, 411008, India.
authors.forename: Rajesh G
authors.initials: RG
authors.lastname: Gonnade
authors.affiliation: Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-, 411008, India. at.biju@ncl.res.in.|Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110020, India. at.biju@ncl.res.in.
authors.forename: Akkattu T
authors.initials: AT
authors.lastname: Biju
keywords: Lewis acids; annulations; arenes; reaction mechanisms; small ring systems