- Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents
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Treatment of N-alkyl-oxazolidin-2-ones with Grignard reagents gives tertiary carboxylic amide products. Various substituted oxazolidinones can be used as illustrated with phenyl, benzyl or isopropyl groups on the 4-position, and methyl, benzyl or p-methox
- Bensa, David,Coldham, Iain,Feinaeugle, Pia,Pathak, Ravindra B.,Butlin, Roger J.
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experimental part
p. 1410 - 1415
(2008/10/09)
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- Efficient preparation of (1′R)-(-)-1-(2′-hydroxy-1′- phenylethyl)piperidin-2-one: Synthesis of (2′S,3R)-(+)-stenusine
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An efficient oxidation of (2′R)-(-)-2′-phenyl-2′- (piperidin-1-yl)ethanol 2 with bromine to generate the corresponding piperidin-2-one 3 in 96% is described. In addition, starting from 3, (2′S,3R)-(+)-stenusine 8 was synthesized in 70% overall yield. The
- Castro-C, Alejandro,Juarez-P, Jorge,Gnecco, Dino,Teran, Joel L.,Galindo, Alberto,Bernes, Sylvain,Enriquez, Raul G.
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p. 949 - 952
(2007/10/03)
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- Reductive and oxidative transformations of the N-(cyanomethyl)oxazolidine system to expand the chiral pool of piperidines
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Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non-racemic N-(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process using potassium permanganate
- Francois, David,Poupon, Erwan,Kunesch, Nicole,Husson, Henri-Philippe
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p. 4823 - 4829
(2007/10/03)
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- Dehydrogenation of cyclic tertiary amines with neighbouring of enantiomeric nucleophiles
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For stereochemical investigation of their dehydrogenation, the enantiomers of the aminoalcohols 1, 2, and 3 were prepared from optically active sources, while the enantiomers of the diamines 8 and 9 were available by resolution of the racemates. The pure antipodes of 1, 2, and 3 reacted with mercury(II)-EDTA by a twofold dehydrogenation via intermediate participation of the neighbouring alcoholic group to the optically active lactams 5, 6, and 7 under complete retention of configuration. In the same manner the diamines 8 and 9 generated by four electron withdrawal the cycloamidines 10 and 11.
- M?hrle, Hans,Berkenkemper, Thomas
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p. 435 - 443
(2007/10/03)
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- Asymmetric synthesis. XXXIX. Synthesis of 3-substituted piperidin-2-ones from chiral non-racemic lactams
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A series of 3-substituted piperidines in enantiomerically pore form has been synthesized from lactam 1 via the bromo derivative 2i. t-Butyl acetate and 5-methylpyridine derivatives 2g and 2h were obtained optically pure by direct alkylation of 1 with corresponding halides. Azido, amino or benzyloxy products were obtained by diastereoselective substitution of 21.
- Micouin,Bonin,Cherrier,Mazurier,Tomas,Quirion -,Husson
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p. 7719 - 7726
(2007/10/03)
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- Asymmetric synthesis. XXX. Synthesis of 3-substituted piperidines from chiral non-racemic lactams
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A series of 3-substituted piperidines in enantiomerically pure form has been synthesized from lactam 3 by a stereospecific route involving a postulated rigid amide enolate. This strategy has been applied to the synthesis of (+)-stenusine 10.
- Micouin, Laurent,Varea, Teresa,Riche, Claude,Chiaroni, Angele,Quirion, Jean-Charles,Husson, Henri-Philippe
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p. 2529 - 2532
(2007/10/02)
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