Concise Total Synthesis of (?)-Vermiculine through a Rhodium-Catalyzed C2-Symmetric Dimerization Strategy
A short and efficient synthesis of the C2-symmetric antibiotic (?)-vermiculine by utilizing an enantioselective catalytic one-step dimerization methodology as key-step to construct the core structure is reported. The late-stage modifications feature a double metathesis homologation followed by a double Wacker-type oxidation. These key-steps allowed the synthesis of vermiculine in only seven steps, starting from commercially available building blocks.
Synthesis of heterocyclic 1,3-oxazolines from aldehydes with trimethylphenylammonium tribromide
Various heterocyclic 1,3-oxazolines were prepared from aldehydes and aminoalcohols with trimethylphenylammonium tribromide at room temperature.
Sayama, Shinsei
p. 979 - 990
(2017/06/13)
Pyridine-oxazoline and quinoline-oxazoline ligated cobalt complexes: Synthesis, characterization, and 1,3-butadiene polymerization behaviors
A series of cobalt complexes supported by pyridine-oxazoline (Pyox) and quinoline-oxazoline (Quox) were synthesized. Determined by single crystal X-ray crystallography, complexes 6a and 7c adopted distorted octahedron and trigonal bipyramid geometries, re
QUINOLINE-OXAZOLINE COMPOUNDS AND THEIR USE IN OXIDATION SYNTHESIS
A quinoline-oxazoline compound having the formula: where one of X1 and X2 is N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline radical having the formula such that when X1 is N R2 is Z and R1 is absent, and when X2 is N either R1 or R3 is Z and R2 is absent. R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with a coordination center. These compounds can be complexed with a suitable coordination center such as catalytically active palladium and can be highly useful in catalytically oxidizing alkenes with high regioselectivity.
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(2011/04/14)
Catalyst-controlled Wacker-type oxidation of protected allylic amines
On the contrary: Utilizing the [Pd-(quinox)]-TBHP catalyst system, protected allylic amines were oxidized with high selectivity for the methyl ketone product. This is contrary to the results obtained by the substrate-controlled Tsuji-Wacker oxidation, which highlights the catalyst-controlled system presented here (see scheme). A variety of N-pro-tecting groups undergo selective oxidation with high ketone selectivity. TBHP = tert-butylhydroperoxide.
Michel, Brian W.,McCombs, Jessica R.,Winkler, Andrea,Sigman, Matthew S.
supporting information; experimental part
p. 7312 - 7315
(2010/11/05)
A general and efficient catalyst system for a wacker-type oxidation using TBHP as the terminal oxidant: Application to classically challenging substrates
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Michel, Brian W.,Camelio, Andrew M.,Cornell, Candace N.,Sigman, Matthew S.
supporting information; experimental part
p. 6076 - 6077
(2009/09/26)
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