Lead Tetraacetate Oxidation of Aminoalcohols

Leonard, Nelson J.; Rebenstorf, Melvin A.

doi:10.1021/ja01217a016

Cited by 22 publications

(4 citation statements)

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“…Nicolet and Shinn had observed that N-diethylaminoethanol, a tertiary hydroxyamine, was not affected by periodic acid (8). Later Leonard and Rebenstorf confirmed the same observation under more strenuous conditions (9). Using a procedure recommended by Siggia (10), we found that diol III consumed about two moles of periodic acid.…”

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confidence: 71%

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SYNTHESES OF SOME 3-PHENYL-3-tert-AMINO-1,2-PROPANEDIOLS

Tsou¹,

Cromwell²

1950

J. Org. Chem.

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Although several investigators have reported the preparation of 1-phenyl-2.amino-1 ,3-propanediols by reacting 1-phenyl-2-bromo-l , 3-propanediol (I) with amines, no proof of the position of the amino group of the resulting diols was given (1, 2). Recently, Controulis, et al. showed that I gave 3-phenyl-3-amino-1,2-propanediol when treated with ammonia (3). It seemed possible that reaction of I with secondary amines may also have led to 3-phenyl-3-tert-amino-1,Zpropanediols. It was thus interesting to reinvestigate such reactions.Another possible approach to the synthesis of l-phenyl-2-tert-amin0-1,3propanediols would be through the reduction of a-amino-p-hydroxy-p-phenylpropionic acids by lithium aluminum hydride. Despite the fact that the literature had indicated that both a-amino and P-amino products were possible when a-bromo-P-hydroxy acids were treated with amines (4), the authors were interested in using a-bromo-P-hydroxy-P-phenylpropionic acid (11) (5) as a starting material in order to correlate these two schemes in their reaction mechanisms.l-Phenyl-2-bromo-l,3-propanediol (I) was prepared in its solid form by using a slightly modified procedure of the early workers (3). On treatment of I with piperidine in water 3-phenyl-3-piperidino-l , 2-propanediol (111) was obtained, associated with one mole of piperidine as solvent of crystallization. 3-Phenyl-3morpholino-l,2-propanediol (IV) was prepared by a similar procedure in low yield.a-Bromo-P-hydroxy-P-phenylpropionic acid (11) reacted with piperidine and morpholine in ether to give the corresponding amine salts (V and VI) of the starting acid. When I1 was treated with the amines in aqueous solution, the unstable piperidine salt (VII) of a-hydroxy-p-piperidino-P-phenylpropionic acid (IX) and the morpholine salt (VIII) of a-hydroxy-8-morpholino-8-phenylpropionic acid (X) were isolated. On drying at 100" VI1 lost piperidine readily to give the free acid (IX). On the other hand, salt VI11 was quite stable. Previously Fourneau ( 6 ) had reported the preparation of acid I X by reacting piperidine with phenylglycidic ester, and had assigned the position of the amino group by referring to an early work of Erlenmeyer (7) who had assigned the structure from its method of synthesis as analogous to that for phenylisoserine. It seemed to us, however, that a melting point alone could not be the conclusive structural evidence in our investigation. The melting point of I X was found to vary widely by inserting the sample at different temperatures of the melting bath. Therefore, the location of the amino group was still doubtful until the latter part of this investigation.

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confidence: 71%

“…Later Leonard and Rebenstorf confirmed the same observation under more strenuous conditions (9). Later Leonard and Rebenstorf confirmed the same observation under more strenuous conditions (9).…”

Section: Kwan-chung Tsou Andsupporting

confidence: 57%

SYNTHESES OF SOME 3-PHENYL-3-tert-AMINO-1,2-PROPANEDIOLS

Tsou¹,

Cromwell²

1950

J. Org. Chem.

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“…The bridgehead aminium radical derived from 1-azaadamantane 23 which is isoelectronic with 14+• as well as the even more strained species from 1-azabicyclo[2.2.2]octane (22) and 1-azabicyclo[2.2.1]heptane (21) have been reported. 173 The 23+• respectively, which compared with aN = 20.7 G for the trimethylaminium radical.…”

Section: Mass Spectroscopymentioning

confidence: 99%

Nonaromatic aminium radicals

Chow¹,

Danen²,

Nelsen³

et al. 1978

Chem. Rev.

246

151

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“…The majority of these methods involve cleavage of a C−H bond at the α-position of an amine substrate [ 7 – 28 ]. Methods that deliver imines through amine α-C−C bond cleavage are far less common [ 29 – 32 ] despite the fact that these methods employ renewable resources, such as amino acids and their derivatives, as starting materials. In fact, only a few reports describing the oxidative deformylation of amino alcohols have been published [ 33 – 35 ], and in all of these reports stoichiometric oxidants, such as NaIO 4 and Pb(OAc) 4 , must be employed to enable the desired transformations.…”

Section: Introductionmentioning

confidence: 99%

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

Liu¹,

Phan²,

Haugeberg³

et al. 2017

Beilstein J. Org. Chem.

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A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C–C bond cleavage.

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Lead Tetraacetate Oxidation of Aminoalcohols

Cited by 22 publications

References 0 publications

SYNTHESES OF SOME 3-PHENYL-3-tert-AMINO-1,2-PROPANEDIOLS

SYNTHESES OF SOME 3-PHENYL-3-tert-AMINO-1,2-PROPANEDIOLS

Nonaromatic aminium radicals

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

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