A New Synthesis of Oxime Derivatives from Carbonyl Compounds and<i>N,O</i>-Bis(trimethylsilyl)hydroxylamine

Hoffman, Robert V.; Buntain, G. A.

doi:10.1055/s-1987-28092

Cited by 13 publications

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“…We initiated our study by examining the cycloaddition of benzaldehyde O -TBS oxime 10 with styrene ( 18a ) as a simple extension to an intermolecular variant. Oxime 10 , on treatment with styrene ( 18a ) (10 equiv) in the presence of 2.2 equiv of BF 3 ·OEt 2 in 1,2-dichloroethane at 60 °C for 24 h, underwent intermolecular cycloaddition via N -boranonitrone F to give the trans -cycloadduct 11 as a single isomer in 40% yield (Scheme ).…”

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confidence: 99%

Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

et al. 2008

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Ethyl glyoxylate O-tert-butyldimethylsilyloxime (8), on treatment with 2.2 equiv of BF3 x OEt2, generated N-boranonitrone E, which underwent intermolecular cycloaddition with alkenes 18 to afford isoxazolidines 19 in moderate to high yields. The cycloaddition of N-boranonitrone E with most of the alkenes gave 3,5-trans isoxazolidines as the major isomers via a concerted mechanism. However, in the case of 1-methylated cyclic alkenes (18j and 18l), the cycloaddition surprisingly furnished the 3,3a-cis-cycloadducts (19j and 19l) as major isomers. A possible explanation is that the reaction of 1-methylated cyclic alkenes proceeds mainly via a stepwise mechanism. This reaction of terminal alkenes is very useful for synthesis of 1,3-anti aminoalcohol derivatives by reductive cleavage of an N-O bond.

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Section: Resultsmentioning

confidence: 99%

Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

et al. 2008

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“…Trimethylsilyloxime ester (4): 1 H NMR (CDCl 3 /TMS) δ 2.31 (m, 2H), 2.24−2.20 (m, 2H), 1.52−1.32 (m, 6H), 0.19 (s, 9H); 13 C NMR (CDCl 3 /TMS) δ 164.4, 32.3, 27.1, 26.0, 25.8, 25.0, −0.7; IR (neat) 2971, 1746, 1463, 1377, 1250 cm -1 .…”

Section: Methodsmentioning

confidence: 99%

An Efficient Synthesis of Dinitrile Derivatives by the Reaction of Oxime Esters or Acid Anhydrides with Cyanotrimethylsilane Catalyzed by La(OⁱPr)₃

2000

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The reaction of oxime esters with cyanotrimethylsilane (Me(3)SiCN) under the influence of a catalytic amount of lanthanide compounds produced alpha-trimethylsilyloxydinitrile derivatives in excellent yields accompanied with the formation of trimethylsilyl oxime ethers. Among the lanthanoid catalysts examined, La(O(i)()Pr)(3) was found to be the best catalyst. The reaction seems to proceed through the formation of acyl cyanides as intermediates, followed by the addition of Me(3)SiCN to them. Additionally, the reaction of acetic anhydride with Me(3)SiCN catalyzed by La(O(i)()Pr)(3) gave 1-trimethylsilyloxyethane dinitrile. Thus, various alpha-trimethylsilyloxydinitriles were synthesized in good yields by allowing oxime esters or acid anhydrides to react with Me(3)SiCN in the presence of a catalytic amount of La(O(i)()Pr)(3).

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“…In a Peterson-type one-pot reaction, oximes and oxime derivatives can be prepared effectively from the N-anion of N,O-bis(trimethylsilyl)hydroxylamine and an aldehyde or ketone (eq 5). 13 Oximes of sterically hindered ketones can be formed in high yields by this procedure. …”

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N,O-Bis(trimethylsilyl)hydroxylamine

Johnson

Hoffman

2001

Encyclopedia of Reagents for Organic Synthesis

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A New Synthesis of Oxime Derivatives from Carbonyl Compounds andN,O-Bis(trimethylsilyl)hydroxylamine

Cited by 13 publications

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Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

An Efficient Synthesis of Dinitrile Derivatives by the Reaction of Oxime Esters or Acid Anhydrides with Cyanotrimethylsilane Catalyzed by La(OⁱPr)₃

N,O-Bis(trimethylsilyl)hydroxylamine

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A New Synthesis of Oxime Derivatives from Carbonyl Compounds andN,O-Bis(trimethylsilyl)hydroxylamine

Cited by 13 publications

References 0 publications

Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

An Efficient Synthesis of Dinitrile Derivatives by the Reaction of Oxime Esters or Acid Anhydrides with Cyanotrimethylsilane Catalyzed by La(OiPr)3

N,O-Bis(trimethylsilyl)hydroxylamine

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An Efficient Synthesis of Dinitrile Derivatives by the Reaction of Oxime Esters or Acid Anhydrides with Cyanotrimethylsilane Catalyzed by La(OⁱPr)₃