Optically Active Amines. IV. The Dissymmetric Chromophore in the N-Salicylidene Derivatives of α- and β-Arylalkylamines<sup>1</sup>

Smith, Howard E.; Willis, T. Chad

doi:10.1021/jo01019a035

Cited by 19 publications

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“…Phenyllithium was used as commercially supplied in cyclohexane-ether. (37), 133 (41), 121 (99), 90 (98), 76 (44). (15), 176 (36), 161 (65), 133 (93), 122 (75), 105 (52), 91 (25).…”

Section: Additions Of Phenyllithiummentioning

confidence: 99%

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Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1

et al. 2004

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A new asymmetric synthesis of alpha-amino acids is described in which the key step is the highly diastereoselective addition of organolithium carboxyl synthons (2-furyllithium, phenyllithium, vinyllithium) to (R)- and (S)-O-(1-phenylbutyl) oximes to give hydroxylamines, with vinyllithium being the most satisfactory nucleophilic reagent. Subsequent reductive cleavage of the N-O bond in hydroxylamines, followed by N-protection, and oxidative cleavage of the carboxyl precursor gave a range of N-protected amino acids and esters. The method was exemplified by the synthesis of a range of derivatives of non-proteinogenic amino acids such as 4-bromophenylalanine, tert-leucine, norvaline, cyclohexyl- and aryl-glycines, 2-amino-8-oxodecanoic acid (Aoda) and alpha-methylvaline.

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“…Phenyllithium was used as commercially supplied in cyclohexane-ether. (37), 133 (41), 121 (99), 90 (98), 76 (44). (15), 176 (36), 161 (65), 133 (93), 122 (75), 105 (52), 91 (25).…”

Section: Additions Of Phenyllithiummentioning

confidence: 99%

“…Obtained by the zinc mediated N-O bond cleavage and subsequent N-protection of hydroxylamine 3e as a colourless solid (28% over two steps, >98% ee); mp 175-176 ЊC (lit., 14 S-enantiomer mp 177-177.5 ЊC); [α] 24 D ϩ42.7 (c 1.03, CHCl 3 ) (lit., 41 [α] 26 D ϩ77; lit., (15), 148 (11), 57 (7).…”

Section: (R )-(؉)-N-acetyl-22-dimethyl-1-phenylpropylamine 4cmentioning

confidence: 99%

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1

et al. 2004

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Recent Applications of Optical Rotatory Dispersion and Optical Circular Dichroism in Organic Chemistry

Crabbé

1967

Topics in Stereochemistry

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The optical rotatory dispersion and circular dichroism of azomethinies

Bonnett

1970

PATAI'S Chemistry of Functional Groups

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Optically Active Amines. IV. The Dissymmetric Chromophore in the N-Salicylidene Derivatives of α- and β-Arylalkylamines¹

Cited by 19 publications

References 0 publications

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1

Recent Applications of Optical Rotatory Dispersion and Optical Circular Dichroism in Organic Chemistry

The optical rotatory dispersion and circular dichroism of azomethinies

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Optically Active Amines. IV. The Dissymmetric Chromophore in the N-Salicylidene Derivatives of α- and β-Arylalkylamines1

Cited by 19 publications

References 0 publications

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1

Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1

Recent Applications of Optical Rotatory Dispersion and Optical Circular Dichroism in Organic Chemistry

The optical rotatory dispersion and circular dichroism of azomethinies

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Optically Active Amines. IV. The Dissymmetric Chromophore in the N-Salicylidene Derivatives of α- and β-Arylalkylamines¹