- Enantioselective Trans Dihydroxylation of Nonactivated C-C Double Bonds of Aliphatic Heterocycles with Sphingomonas sp. HXN-200
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The bacterial strain Sphingomonas sp. HXN-200 was used to catalyze the trans dihydroxylation of N-substituted 1,2,5,6-tetrahydropyridines 1 and 3-pyrrolines 4 giving the corresponding 3,4-dihydroxypiperidines 3 and 3,4-dihydroxypyrrolidines 6, respectivel
- Chang, Dongliang,Heringa, Maarten F.,Witholt, Bernard,Li, Zhi
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- Asymmetric desymmetrization of meso-pyrrolidine derivatives by enantiotopic selective C-H hydroxylation using (salen)manganese(III) complexes
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Chiral (salen)manganese(III) complexes 1 catalyzed the asymmetric desymmetrization of N-protected meso-pyrrolidine derivatives 3, 6-8, 15 and 18 by enantiotopic selective C-H oxidation in the presence of terminal oxidant iodosylbenzene. The oxidation occurred chemoselectively at the carbon α to the nitrogen atom to afford optically active hydroxypyrrolidine derivatives 9, 11, 13, 16, 19 and 21 that were further oxidized to chiral lactams with Jones reagent. The N-protecting groups of the meso-pyrrolidine derivatives have notable effect on the enantioselectivity.
- Punniyamurthy,Katsuki, Tsutomu
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p. 9439 - 9454
(2007/10/03)
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