Oxidations of Organic Compounds with Osmium Tetroxide

Singh, Hari Shankar

doi:10.1007/978-1-4613-2109-5_12

Cited by 12 publications

(2 citation statements)

References 190 publications

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“…The aforedescribed diol 10 was converted into alkene 31 uneventfully by the Corey−Winter reaction in 64% overall yield (Scheme 7). cis -Dihydroxylation of a 10 -2 M solution of the alkene 31 via osmium tetraoxide catalysis resulted in 20% yield of the desired β-diol 32 , 10% of α-diol 10 , and 60% of the starting alkene 31 . The stereochemistry of the β-1,2-diol 32 was supported by the 1 H NMR coupling constant data ( J 1,2 = 3.2, J 1,7eq = 2.7, J 1,7ax = 2.8, J 2,3 = 9.2 Hz).…”

Section: Resultsmentioning

confidence: 99%

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Shing

Wan

1996

J. Org. Chem.

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Valiolamine (1), 1-epi-valiolamine (2), 2-epi-valiolamine (3), (1R,2R)-valiolamine (4), and 2-amino regioisomer 17 have been prepared from (−)-quinic acid (6) in 14 (8.4% overall yield), 13 (9.0%), 15 (4.3%), 17 steps (2.5%), and 12 steps (13%), respectively. Charged nucleophilic ring-openings of cyclic sulfate (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohexane-1,2,3,4,5-pentol (11) occurred regioselectively at C-2, whereas the corresponding ring-openings of its (1S,2R)-diastereomer 34 proceeded preponderantly at C-1. (1R,2S,3R,4S,5S)-2,4,5-Tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol (24) underwent novel internal displacement spontaneously to form (1S,2S,3R,4S,5S)-1,2,4-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-1,2,3,4,5-pentol (25), whereas its 2-epimer was inert under the same conditions. Ruthenium-catalyzed dihydroxylation of alkene, (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol (31), gave the desired β-1,2-diol 32 in higher yield and stereoselectivity than the osmium tetraoxide protocol. The regioselectivity of charged nucleophilic ring-openings of cyclic sulfates 11, 34, and 38 is discussed.

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Section: Resultsmentioning

confidence: 99%

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Shing

Wan

1996

J. Org. Chem.

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“…Osmium tetroxide (OsO 4 ) is the most reliable reagent for dihydroxylation of olefins to give the corresponding vicinal diols . The reaction proceeds in the presence of a catalytic amount of OsO 4 using a cooxidant such as metal chlorates, hydrogen peroxide, tert -butyl hydroperoxide, potassium ferricyanide, or most commonly, N -methylmorpholine N -oxide (NMO).…”

Section: Polystyrene-based Catalystsmentioning

confidence: 99%

“Microencapsulated” and Related Catalysts for Organic Chemistry and Organic Synthesis

2009

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Sodium Periodate-Osmium Tetroxide

Wee¹,

Liu²

2001

Encyclopedia of Reagents for Organic Synthesis

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Oxidations of Organic Compounds with Osmium Tetroxide

Cited by 12 publications

References 190 publications

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

“Microencapsulated” and Related Catalysts for Organic Chemistry and Organic Synthesis

Sodium Periodate-Osmium Tetroxide

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Oxidations of Organic Compounds with Osmium Tetroxide

Cited by 12 publications

References 190 publications

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.1 Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.1 Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

“Microencapsulated” and Related Catalysts for Organic Chemistry and Organic Synthesis

Sodium Periodate-Osmium Tetroxide

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Product

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Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Facile Syntheses of Valiolamine and Its Diastereomers from (−)-Quinic Acid.¹ Nucleophilic Substitution Reactions of 5-(Hydroxymethyl)cyclohexane-1,2,3,4,5-pentol