Nitrosocarbonyl compounds as intermediates in the oxidative cleavage of hydroxamic acids

Kirby, G. W.; Sweeny, James G.

doi:10.1039/c39730000704

Cited by 76 publications

(67 citation statements)

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“…Carboxamide N-oxide (acyl nitroso) compounds are particularly reactive nitroso compounds which are usually generated and directly trapped by dienes. 35 An intriguing concept for enantioselective nitroso HDA reaction was reported by Whiting and co-workers. They found that the oxidation of hydroxamic acids catalyzed by the oxoruthenium complex afforded corresponding acyl nitroso compounds which reacted with dienes simultaneously.…”

Section: Enantioselective Nitroso Hetero-diels-alder Reactionmentioning

confidence: 99%

Nitroso and Azo Compounds in Modern Organic Synthesis: Late Blooming but Very Rich

Yamamoto

Kawasaki

2007

Bulletin of the Chemical Society of Japan

161

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The catalytic enantioselective oxidation is an extremely important process in organic synthesis and numbers of effort to improve this process have been reported so far. Although nitroso and azo compounds are attractive tools for hydroxylation and amination of organic compounds, no reports on a catalytic asymmetric version of these reactions had been reported until recently. The main issues were their high and unique reactivities. In this review, we would like to introduce the recent advances in this area.

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Section: Enantioselective Nitroso Hetero-diels-alder Reactionmentioning

confidence: 99%

Nitroso and Azo Compounds in Modern Organic Synthesis: Late Blooming but Very Rich

Yamamoto

Kawasaki

2007

Bulletin of the Chemical Society of Japan

161

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“…Coupling constants are very characteristic in the inverse adducts 7 ( Table 4): 3J (3,4) and 3J (5,6) are ca. 4 .…”

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confidence: 98%

“…-In two preceding publications, we described the stereospecific syntheses of some racemic amino-deoxysugar derivatives which belong to the lyxose [l], and to the ribose and allose series [2]. In all cases, the first step was a hetero-Diels-Alder cycloaddition of the dienes 1 and 2 with acylnitroso dienophiles 4 ( R = RCO), the latter being prepared by in situ oxidation of the corresponding hydroxamic acids 3 with (Pr,N)IO, [3]. cis-Hydroxylation of the primary cycloadducts with OsO,, followed by reductive cleavage of the N-0 bond led to the target molecules, i.e.…”

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confidence: 99%

From 1‐(Silyloxy)Butadiene to 4‐Amino‐4‐Deoxy‐DL‐Erythrose and to 1‐Amino‐1‐Deoxy‐DL‐Erythritol Derivatives via Hetero‐Diels‐Alder Reactions with Acylnitroso Dienophiles

Defoin

Pires

Streith

1991

Helvetica Chimica Acta

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~~~~~~~ ~~~ ~Acylnitroso dienophiles 4 reacted instantly with I-(si1yloxy)butadiene 5a and led in good yield to the regioisomeric cycloadducts 6 (major) and 7 (minor; Scheme 2, Table I ) . cis-Hydroxylation of these primary cycloadducts with OsO, (catalyst) occurred stereospecifically and in high yield ( 4 and 9, resp.; Scheme 2). It was followed by reductive ring cleavage to give either I-amino-1 -deoxy-m-erythritol or 4-amino-4-deoxy-~~-erythrose derivatives 10 and 14, respectively, depending on the nature of the reducing agent (Schemes 3 and 4 ) .Introduction. -In two preceding publications, we described the stereospecific syntheses of some racemic amino-deoxysugar derivatives which belong to the lyxose [l], and to the ribose and allose series [2]. In all cases, the first step was a hetero-Diels-Alder cycloaddition of the dienes 1 and 2 with acylnitroso dienophiles 4 ( R = RCO), the latter being prepared by in situ oxidation of the corresponding hydroxamic acids 3 with (Pr,N)IO, [3]. cis-Hydroxylation of the primary cycloadducts with OsO,, followed by reductive cleavage of the N-0 bond led to the target molecules, i.e. the aminosugars.In the lyxose series, both regioisomeric Diels-Alder cycloadducts were formed, in a ratio which depended upon the acylnitroso R group. The formation of these pairs of regioisomers was best explained by frontier MO interaction (FMO theory) between the diene and the dienophile partners [l]. In the ribose and allose series, the cycloadditions were regiospecific; in our opinion, this is best explained by a steric effect which overrides the orbital interaction [2].We describe herein the synthesis of some racemic 4-amino-4-deoxy-erythrose and 1 -amino-1 -deoxy-erythritol derivatives by a similar approach to the one cited above, the starting material being the 1-(sily1oxy)butadiene 5a. This diene had already been described [4] and was easily obtained using either one of the following procedures: i) crotonaldehyde and silyl chloride in benzene solution in the presence of Et,N and ZnC1,

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“…-In a previous publication, we described the three-step synthesis of the aminolyxose derivatives 2 and 3, starting from the readily accessible 1,2-dihydropyridine derivative 1 [l] (Scheme I ) . The first step was a Diels-Alder reaction between 1 and a series of acylnitroso dienophiles 5 which were prepared in situ by oxidation of the corresponding hydroxamic acids 6 using tetraalkylammonium periodates [2]. Some of these dienophiles reacted in a regiospecific manner; some others proved to be slightly or not at all regioselective.…”

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confidence: 99%

Syntheses of Amino‐dideoxyallose and Amino‐deoxyribose Derivatives Using Acylnitroso Dienophiles

Defoin

Fritz

Geffroy

et al. 1988

Helvetica Chimica Acta

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Dedicated to Professor Elius J. Corey on the occasion of his 60th birthday (26.V11.88)The dimethyl acetals 4 of (E)-2,4-pentadienal and of (E,E)-and (E,Z)-2,4-hexadienals undergo regio-and stereospecific cycloaddition reactions with in-situ-generated acylnitroso dienophiles Sa and Sb, leading thereby to the corresponding dihydrooxazines 7a-d and 8c-d. cis-Glycolization of these latter adducts stereospecifically gave the dihydro derivatives 9a-d and 10d which, after sequential hydrogenolysis, deacetalization, and instant cyclization, led to the aminodeoxyribose derivatives 17a, 17f, and 18, and to the amino-dideoxyallose compounds 17c and 17b. These piperidino-deoxysugar derivatives exhibit a strong anomeric effect, i.e. OH-C( 1) is always axial, which is explained in terms of a n,(n)-o*(C-OH) orbital compression, as compared to the less pronounced one in the more classical pyranose series.

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Nitrosocarbonyl compounds as intermediates in the oxidative cleavage of hydroxamic acids

Cited by 76 publications

References 0 publications

Nitroso and Azo Compounds in Modern Organic Synthesis: Late Blooming but Very Rich

Nitroso and Azo Compounds in Modern Organic Synthesis: Late Blooming but Very Rich

From 1‐(Silyloxy)Butadiene to 4‐Amino‐4‐Deoxy‐DL‐Erythrose and to 1‐Amino‐1‐Deoxy‐DL‐Erythritol Derivatives via Hetero‐Diels‐Alder Reactions with Acylnitroso Dienophiles

Syntheses of Amino‐dideoxyallose and Amino‐deoxyribose Derivatives Using Acylnitroso Dienophiles

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