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Total synthesis of (+/-)-goniomitine via a formal nitrile/donor-acceptor cyclopropane [3 + 2] cyclization.
The total synthesis of (+/-)-goniomitine has been accomplished in 17 linear steps with 5.2% overall yield starting from commercially available delta-valerolactam and the use of a microwave reactor is shown to greatly improve the reaction times for two steps.
First total synthesis and structural reassignment of (-)-aplysiallene.
The first total synthesis of (-)-aplysiallene has been completed in 16 steps and features a key sequential Mukaiyama aerobic oxidative cyclization to prepare the fused bis-THF core. The original…
Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.
Lewis acids control regioselectivity in the alkylation of epi-chlorohydrin and the stereochemistry of an alkyne addition to set the C24/C23 anti relationship. These advances facilitate an efficient…
The Regioselective Mono-deprotection of 1,3-Dioxa-2,2-(di-tert-butyl)-2-silacyclohexanes with BF3×SMe2.
Substrate and reagent control of diastereoselectivity in transition metal mediated processes : development of a catalytic photopromoted Pauson-Khand reaction
- B. Pagenkopf
Recent advances in donor-acceptor (DA) cyclopropanes
Cycloadditions of Donor–Acceptor Cyclopropanes and Nitriles
Lewis acid promoted cycloaddition reactions of donor–acceptor (DA) cyclopropanes are one of the well-studied approaches for the construction of heterocyclic and carbocyclic frameworks. During our…
C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.
- B. Bajtos, Ming‐Shiuan Yu, Hongda Zhao, B. Pagenkopf
- Chemistry, BiologyJournal of the American Chemical Society
- 14 July 2007
The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters and a single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters is reported.
Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes.
- Tristan Chidley, Naresh Vemula, C. Carson, M. Kerr, B. Pagenkopf
- ChemistryOrganic letters
- 7 June 2016
Tandem ring opening, elimination, and cycloaddition of donor-acceptor cyclopropanes were observed in Yb(OTf)3-catalyzed cycloaddition with nitrosoarenes. The reaction results in formation of…
The formal [4+3] cycloaddition between donor-acceptor cyclobutanes and nitrones.
The formal [4+3] cycloaddition of 2-alkoxy-1,1-dicarboxylate activated donor-acceptor cyclobutanes with nitrones is disclosed. The reaction forms structurally unique oxazepines in moderate to high…