The Synthesis of Vicinal Amino Alcohols

Bergmeier, Stephen C.

doi:10.1016/s0040-4020(00)00149-6

Cited by 892 publications

(453 citation statements)

References 126 publications

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“…[1][2][3][4][5][6][7] For example, some have been found to act as HIV protease inhibitors [1][2][3] and still others have been shown to exert renin inhibitor activity. 5,6 Aminodiols are also useful starting materials for the syntheses of oxazines or oxazolidines, depending upon which hydroxy group undergoes ring closure with the amino group.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of enantiomeric spirooxazolines and spirooxazolidines by the regioselective ring closure of (–)-α-pinene-based aminodiols

Szakonyi¹,

Hetényi²,

Fülöp³

2007

Arkivoc

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Starting from (1R,2S,3S,5R)-2-benzylaminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol (4) and (1R,2S,3S,5R)-2-aminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol (5), spirooxazolines and spirooxazolidines were prepared. In the reactions of 4 and 5 with alkyl or aryl isothiocyanate, the ring closure proceeded regioselectively and resulted only in spiro derivatives of 2-aryl-and alkyliminooxazolidines 12-17. The primary aminodiol 5 was transformed with ethyl 4-chlorobenzimidate to a spiro-2-(4-chlorophenyl)oxazoline 18 in a highly regioselective ring closure. The reaction of 5 with formaldehyde resulted in tetracyclic compound 19.

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Section: Introductionmentioning

confidence: 99%

Synthesis of enantiomeric spirooxazolines and spirooxazolidines by the regioselective ring closure of (–)-α-pinene-based aminodiols

Szakonyi¹,

Hetényi²,

Fülöp³

2007

Arkivoc

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“…1 H, 13 C and the detailed 2D NMR spectra were determined on Varian Mercury Plus 400 spectrometer. Chemical shifts are reported in parts per million using solvent as the internal standard (DMSO-d6).…”

Section: Methodsmentioning

confidence: 99%

Epoxide ring-opening approach to the synthesis of diverse trisubstituted cyclopentanes

Larin¹,

Atroshchenko²

2016

Arkivoc

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The regiospecificity of the epoxide ring-opening reactions of (1RS,2SR,3SR)-1,2-epoxy-3-(Nbenzyl-N-methylamino)-cyclopentane 1 and (1RS,2SR,3SR)-1,2-epoxy-3-(N,N-dibenzylamino)-cyclopentane 2 with O-and C-nucleophiles has been explored. It has been shown that electronic and steric factors could affect the regioisomeric ratio of the products due to the possibility for a nucleophile to attack both oxirane carbon atoms. New mimics of 2-deoxystreptamine (2-DOS), the main structural motif of aminoglycoside type antibiotics, have been synthesized.

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“…3 Due to the cost and toxicity of osmium salts, however, a variety of alternate methods for olefin oxyamination have been developed that utilize palladium 4 and copper 5 catalysts. We previously reported that N-sulfonyl oxaziridines ("Davis' oxaziridines") 6 react with olefins in the presence of copper(II) catalysts to afford 1,3-oxazolidines.…”

Section: Introductionmentioning

confidence: 99%

Iron-Catalyzed Aminohydroxylation of Olefins

2010

Synfacts

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We have discovered that N-sulfonyl oxaziridines react with a broad range of olefins in the presence of iron salts to afford 1,3-oxazolidines. This process provides access to 1,2-aminoalcohols with the opposite sense of regioselectivity produced from the copper-catalyzed oxyamination previously reported from our labs. Thus, either regioisomeric form of 1,2-aminoalcohols can easily be obtained from the reaction of oxaziridines with olefins, and the sense of regioselectivity can be controlled by the appropriate choice of inexpensive, non-toxic first row transition metal catalyst.The osmium-catalyzed Sharpless aminohydroxylation 1,2 is a powerful method for the rapid transformation of alkenes into 1,2-aminoalcohols. 3 Due to the cost and toxicity of osmium salts, however, a variety of alternate methods for olefin oxyamination have been developed that utilize palladium 4 and copper 5 catalysts. We previously reported that N-sulfonyl oxaziridines ("Davis' oxaziridines") 6 react with olefins in the presence of copper(II) catalysts to afford 1,3-oxazolidines. 7 In this communication, we report that iron salts 8 are also effective catalysts for oxaziridine-mediated oxyamination but provide the opposite regiomeric outcome. Thus, the appropriate choice of inexpensive, nontoxic first-row transition metal in this transformation enables complementary access to 1,2-aminoalcohols in either regioisomeric form.

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The Synthesis of Vicinal Amino Alcohols

Cited by 892 publications

References 126 publications

Synthesis of enantiomeric spirooxazolines and spirooxazolidines by the regioselective ring closure of (–)-α-pinene-based aminodiols

Synthesis of enantiomeric spirooxazolines and spirooxazolidines by the regioselective ring closure of (–)-α-pinene-based aminodiols

Epoxide ring-opening approach to the synthesis of diverse trisubstituted cyclopentanes

Iron-Catalyzed Aminohydroxylation of Olefins

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