39672-01-0Relevant academic research and scientific papers
A Complementary Process to Pauson-Khand-Type Annulation Reactions for the Construction of Fully Substituted Cyclopentenones
Millham, Adam B.,Kier, Matthew J.,Leon, Robert M.,Karmakar, Rajdip,Stempel, Zachary D.,Micalizio, Glenn C.
, p. 567 - 570 (2019)
A complementary process to the Pauson-Khand annulation is described that is well suited to forging densely substituted/oxygenated cyclopentenone products (including fully substituted variants). The reaction is thought to proceed through a sequence of meta
Tertiary Enamide-Triggered SEAr: Domino Allylation and Enamine-Type Addition
Beltran, Frédéric,Miesch, Laurence
supporting information, p. 1569 - 1573 (2019/03/12)
Two unprecedented domino reactions are described, starting from ketospiro-enesulfonamides. By treatment with ZrCl4 and allylsilane, an intramolecular electrophilic aromatic substitution and subsequent allylation is observed. By treatment with TiCl4 and allylsilane, a double enamine-type reaction takes place, thus creating simultaneously four contiguous stereogenic centers diastereoselectively.
The asymmetric alkylation of dimethylhydrazones; Intermolecular chirality transfer using sparteine as chiral ligand
McSweeney, Christina M.,Foley, Vera M.,McGlacken, Gerard P.
supporting information, p. 14817 - 14819 (2014/12/11)
The asymmetric alkylation of ketones represents a fundamental transformation in organic chemistry. Chiral auxiliaries have been used almost exclusively for this transformation. Herein we describe a strategy for the generation of enantiomerically enriched α-alkylated ketones up to an er of 83:17, using a chiral ligand protocol. This journal is
Intramolecular reductive ketone-alkynoate coupling reaction promoted by (η2-propene)titanium
Schaefer, Christian,Miesch, Michel,Miesch, Laurence
supporting information; scheme or table, p. 3253 - 3257 (2012/06/01)
Intramolecular reductive coupling of cycloalkanones tethered to alkynoates in the presence of (η2-propene)titanium was successfully performed to provide hydroxy-esters in a diastereoselective manner. Subsequent lactonization afforded angularly
Gold-catalyzed 1,3-acyloxy migration/5-exo-dig cyclization/1,5-acyl migration of diynyl esters
Lebuf, David,Simonneau, Antoine,Aubert, Corinne,Malacria, Max,Gandon, Vincent,Fensterbank, Louis
supporting information; experimental part, p. 6868 - 6871 (2011/08/06)
Working three shifts: Polyconjugated δ-diketones are formed stereoselectively in high yields by the gold-catalyzed rearrangement of 1,6-diyn-3-yl esters. This cascade involves a 1,3-sigmatropic acyloxy shift, a 5-exo-dig cyclization of the resulting allenyne, and an unprecedented 1,5-sigmatropic shift of an acyl fragment. The usefulness of the products was shown by an efficient acid-catalyzed transformation into a complex polycyclic framework. Copyright
The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction
Macleod, Fraser,Lang, Stuart,Murphy, John A.
supporting information; experimental part, p. 529 - 534 (2010/10/02)
2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example. Georg Thieme Verlag Stuttgart.
Photoinduced atom-transfer cyclization of α-iodocycloalkanones bearing an allenyl side chain
Lin, Hsien-Hsun,Chang, Wen-Sheng,Luo, Shun-Yuan,Sha, Chin-Kang
, p. 3289 - 3292 (2007/10/03)
(Chemical Equation Presented) Irradiation of α-iodocycloalkanones bearing an allenyl side chain with a sunlamp effected atom-transfer cyclization to give cyclized products in good yield. A mechanism, involving radical atom-transfer cyclization accompanied
New cascade reactions starting from acetylenic ω-ketoesters: An easy access to electrophilic allenes and to 1,3-bridgehead ketones
Klein, Aurélie,Miesch, Michel
, p. 4483 - 4485 (2007/10/03)
Acetylenic ω-ketoesters bearing a three carbon-carbon bond spacer reacted smoothly with tetra-n-butylammonium fluoride and with potassium tert-butoxide to afford either electrophilic allenes or 1,3-bridgehead ketones, the latter being potentially useful m
Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones
Morisson,Barnier,Blanco
, p. 7749 - 7764 (2007/10/03)
Optically active α-methyl α-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives.
