- Controlled reduction of 5-alkyl-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2- a]pyridin-4-ylium iodide: Enantioselective synthesis of (-)-dihydropinidine and (+)-indolizidine 167B
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A controlled reduction of (+)-(3R,5S)-5-methyl- and (+)-(3R,5S)-5-n-propyl- 3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide 1 and 2 to generate (3R,5S)-5-methyl- and (3R,5S)-5-n-propyl-3-phenyl-2,3,5,6,7,8- hexahydro-oxazolo[3,2-a]pyri
- Roa, Luis F.,Gnecco, Dino,Galindo, Alberto,Teran, Joel L.
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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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- Facile diastereoselective reactions of chiral 1,3-oxazolidines with grignard reagents; asymmetric syntheses of 2-substituted and 2,6-disubstituted piperidines
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(S)- and (R)-2-Phenylpiperidines, (S)- and (R)-2-methylpiperidines, meso- and (2R, 6R)-2,6-diphenylpiperidines, and meso- and (25, 65)-2,6-dimethylpiperidines were synthesized asymmetrically starting from the diastereoselective addition of Grignard reagents to chiral 1,3-oxazolidines, converting of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives as pivotal intermediates.
- Poerwono, Hadi,Higashiyama, Kimio,Yamauchi, Takayasu,Takahashi, Hiroshi
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p. 385 - 400
(2007/10/03)
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