111649-71-9Relevant academic research and scientific papers
Rhodium-catalyzed endo -selective epoxide-opening cascades: formal synthesis of (-)-brevisin
Armbrust, Kurt W.,Beaver, Matthew G.,Jamison, Timothy F.
supporting information, p. 6941 - 6946 (2015/06/16)
[Rh(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Synth
Diversity-oriented synthesis of hydrazine-derived compounds from amino isocyanates generated in situ
Clavette, Christian,Vincent Rocan, Jean-Francois,Beauchemin, Andre M.
supporting information, p. 12705 - 12708 (2013/12/04)
Behind the mask: Nitrogen-substituted isocyanates are rare and their synthetic potential is virtually untapped. Simple masked precursors can form amphoteric amino isocyanate intermediates in situ, and allows the synthesis of complex hydrazine derivatives upon addition with amines. This reactivity was used in a cascade substitution/hydroamination sequence, and in the assembly of azadipeptide analogues. Copyright
Studies Directed toward the Total Synthesis of Azaspiracid: Stereoselective Construction of C1-C12, C13-C19, and C21-C25 Fragments
Carter, Rich G.,Weldon, David J.
, p. 3913 - 3916 (2007/10/03)
equation presented The efficient entry to the C1-C12, C13-C19, and C21-C25 fragments of azaspiracid is outlined. The C1-C12 portion is constructed using a key asymmetric allenyl borane addition to the corresponding α,β-unsaturated aldehyde. The synthesis of the C13-C19 portion utilizes an Evans asymmetric alkylation followed by Sharpless asymmetric dihydroxylation. In addition, a novel solution to the mismatched effects of a neighboring chiral oxazolidinone during a Sharpless dihydroxylation is detailed.
Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes
Nacro,Baltas,Gorrichon
, p. 14013 - 14030 (2007/10/03)
Aldol condensations on α,β-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and syn γ,δ-epoxy β-hyd
Tandem radical cyclizations on lodoaryl azides: synthesis of the core tetracycle of aspidosperma alkaloids
Kizil, Murat,Patro, Balaram,Callaghan, Owen,Murphy, John A.,Hursthouse, Michael B.,Hibbs, Dai
, p. 7856 - 7862 (2007/10/03)
A new stereoselective approach to the tetracyclic core of Aspidosperma alkaloids is described. Selective attack by tristrimethylsilylsilyl radicals on the aryl carbon-iodine bond of iodoaryl azides was first demonstrated on the simple model 15, thus both extending the recent discoveries of Kim and co-workers on aliphatic C-I bonds and demonstrating that the selectivity can be exploited in cascade radical cyclizations. Extension to the more complex substrate 25 afforded the core ABCE tetracyclic skeleton of the alkaloids in excellent yield and with efficient control of relative stereochemistry.
Intramolecular termination of radical-polar crossover reactions
Murphy, John A.,Rasheed, Faiza,Roome, Stephen J.,Scott, Karen A.,Lewis, Norman
, p. 2331 - 2339 (2007/10/03)
Cyclic ethers result from intramolecular trapping of cations formed through the radical-polar crossover process.
Termination of radical-polar crossover reactions by intramolecular nucleophiles
Murphy, John A.,Rasheed, Faiza,Roome, Stephen J.,Lewis, Norman
, p. 737 - 738 (2007/10/03)
Radical-polar crossover reactions featuring intramolecular nucleophilic termination are reported.
A Stereoselective Route to Vicinally Substituted Cyclopentane- and Cyclobutane-carboxylates
Kim, Deukjoon,Jang, Yoo Mi,Kim, In O,Park, Sang Woo
, p. 760 - 761 (2007/10/02)
Intramolecular alkylation of the enolates derived from the esters (3) and (7) stereoselectively afforded the cyclopentanecarboxylate (4) and the cyclobutanecarboxylate (8), respectively; compound (8) is a potential intermediate for the synthesis of (+/-)-
