116608-34-5Relevant academic research and scientific papers
Oxyallyl Cation Capture via Electrophilic Deborylation of Organoboronates: Access to α, α′-Substituted Cyclic Ketones
Nguyen, Truong N.,Setthakarn, Krit,May, Jeremy A.
supporting information, p. 7837 - 7840 (2019/10/16)
An umpolung strategy to synthesize α,α′-substituted cyclic ketones through the nucleophilic addition of organoboronates to α-hydroxyl silyl enol ethers is described. The reaction proceeds via the trapping of in situ generated oxyallyl cations via the electrophilic deborylation of C(sp2) and C(sp) borates. This efficient and straightforward method provides direct access to α-substituted silyl enol ethers in high yield with complete regioselectivity. Desilylation in a one-pot procedure provides the corresponding α,α′-disubstituted ketones with high diastereoselectivity.
Synthesis of fused oxabicyclic systems by metal-catalyzed intramolecular addition of 1,3-cycloalkyldiones to alkynes
Gulias, Moises,Rodriguez, J. Ramon,Castedo, Luis,Mascarenas, Jose L.
, p. 1975 - 1977 (2007/10/03)
(Matrix presented) Readily available 4-propargyl-1,3-cyclohexanediones and cyclopentanediones can be chemo- and regioselectively cycloisomerized to synthetically appealing fused oxabicyclic systems by simply stirring at room temperature with catalytic amounts of an appropriate metal complex.
Synthesis of eight- and nine-membered carbocycles through a ring-closing metathesis/ring fragmentation strategy: A rapid and versatile approach to bicyclo[6.4.0]- and Bicyclo[7.4.0]alkene Ring systems
Rodriguez, J. Ramon,Castedo, Luis,Mascarenas, Jose L.
, p. 2923 - 2930 (2007/10/03)
Ring-closing metathesis (RCM) of cis-2,6-dialkenyl-2-hydroxy-1-cyclohexanones affords bicyclo[3.-n.1]alkenones that are easily converted into eight- or nine-membered carbocycles by oxidative cleavage of the keto-bridging tether. Since the starting cyclo-h
An expeditious route to eight- and nine-membered carbocycles based on a RCM-ring fragmentation strategy
Rodríguez, J. Ramón,Castedo, Luis,Mascare?as, José L.
, p. 3209 - 3212 (2007/10/03)
(matrix presented) The presence of a temporary one-atom internal tether in 1,9-deca- and 1,10-undecadienes allows their efficient ring-closing metathesis (RCM). Cleavage of the bridging tether of the resulting bicycles provides eight-or nine-membered carb
Synthesis and intramolecular photocycloadditions of 2-acyloxy-3-hexenoyl cyclohexenones: Diastereoselectivity in the intramolecular [2+2] photocycloadditions of alkenes and cyclohexenones tethered by four atoms
Crimmins, Michael T.,King, Bryan W.,Watson, Paul S.,Guise, Lisa E.
, p. 8963 - 8974 (2007/10/03)
The intramolecular [2+2] photocycloaddition of 2-acyloxy-2-3- hexenoylcyclohexenones has been shown to be highly diastereoselective. The cycloadditions produce exclusively cis fused products and the sense and level of selectivity is consistent with a molecular mechanics model for initial bond formation in the stepwise cycloaddition.
CONVERGENT APPROACH TO INTERMEDIATES USED FOR THE SYNTHESIS OF THE ENEDIYNE STRUCTURE OF THE ESPERAMICINS AND CALICHEAMICINS
Kadow, J. F.,Saulnier, M. G.,Tun, M. M.,Langley, D. R.,Vyas, D. M.
, p. 3499 - 3500 (2007/10/02)
The diynene lithium acetylide 5 adds to 2-siloxy-2-cyclohexenone 6 followed by silyl migration to produce ketone adduct 7, an intermediate towards a simple Esperamicin core
Intramolecular Free Radical Cyclisations onto Enol Ethers. A General Synthesis of α-Alkyl-β-oxy- and α-Methylene-β-oxy-γ-butyrolactones
Begley, Michael J.,Landlow, Mark,Pattenden, Gerald
, p. 1095 - 1106 (2007/10/02)
Radical cyclisation of the enol ether bromoacetals (26), (28a-c), (29), and (37) in the presence of tributylstannane, produces precursors to the β-oxy-γ-butyrolactones (33), (34a-c), (35), and the α-methylene-β-oxy-γ-butyrolactone (39) in high overall yields.By contrast, treatment of (26) and (28a-b) with the cobalt(I) reagent derived from bis(dimethylglyoximato)(pyridine)cobalt(III) chloride (40), followed by oxidation of the intermediates (43) leads to the corresponding unsaturated β-oxy-γ-butyrolactones (42).
