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Volumn 74, Issue 13, 2009, Pages 4655-4665

Catalytic, one-pot synthesis of β-amino acids from α-amino acids. Preparation of α,β-peptide derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACYLIMINIUM ION; AMINO ACID DERIVATIVES; CHEMICAL EQUATIONS; GOOD YIELD; ONE POT; ONE-POT SYNTHESIS; OXIDATION REACTIONS; SEQUENTIAL PROCESS; TRI-PEPTIDES;

EID: 67649616327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9004487     Document Type: Article
Times cited : (50)

References (126)
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    • The radical scission can also be promoted by heating, but visible light irradiation allows milder reaction conditions. To set an irradiation standard, 80 W tungsten-filament lamps (from DIY shops) were used herein
    • The radical scission can also be promoted by heating, but visible light irradiation allows milder reaction conditions. To set an irradiation standard, 80 W tungsten-filament lamps (from DIY shops) were used herein.
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    • For reviews on the Mannich reaction and related processes, see
    • (a) For reviews on the Mannich reaction and related processes, see: Ferraris, D. Tetrahedron 2007, 63, 9581-9597.
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    • For some reviews, see: Juaristi, E., Soloshonok, V. A., Eds.; Wiley-VCH: New York
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    • 2O, 70°C). While this methodology is very useful in laboratory scale to prepare α-unsubstituted and even α-monosubstituted β-amino acids, it is not suitable for large-scale synthesis, due to the expensive silver catalyst and the hazardous diazoalkyl reagents. See
    • 2O, 70°C). While this methodology is very useful in laboratory scale to prepare α-unsubstituted and even α-monosubstituted β-amino acids, it is not suitable for large-scale synthesis, due to the expensive silver catalyst and the hazardous diazoalkyl reagents. See: Belsito, E.; Gioia, M. L.; Greco, A.; Leggio, A.; Liguori, A.; Perri, F.; Siciliano, C.; Viscomi, M. C. J. Org. Chem. 2007, 72, 4798-4802.
    • (2007) J. Org. Chem. , vol.72 , pp. 4798-4802
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    • Other methods were also tried, but they are not mentioned in the sake of clarity. For instance, a method using DIB (1.5 equiv) and iodine (0.5 equiv) gave similar results to Method A [DIB (1.5 equiv), iodine (0.3 equiv)]
    • Other methods were also tried, but they are not mentioned in the sake of clarity. For instance, a method using DIB (1.5 equiv) and iodine (0.5 equiv) gave similar results to Method A [DIB (1.5 equiv), iodine (0.3 equiv)].
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    • (1983) Reactive Intermediates , vol.3 , pp. 367-426
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    • The ring adopts preferentially an envelope conformation, with the acetoxy group in a pseudoaxial position, and the nucleophile adds from the inside face of the envelope, giving the cis product. The attack from the outside face is disfavored, due to the eclipsing interactions developed between the substituents at C-2 and C-3 in the transition structure for the trans product
    • (a) The ring adopts preferentially an envelope conformation, with the acetoxy group in a pseudoaxial position, and the nucleophile adds from the inside face of the envelope, giving the cis product. The attack from the outside face is disfavored, due to the eclipsing interactions developed between the substituents at C-2 and C-3 in the transition structure for the trans product.
  • 115
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    • The addition of methanol after the scission step was necessary to obtain good yields. If the fragmentation was followed by addition of the nucleophile and the Lewis acid, a complex product mixture was formed. The addition of methanol probably deactivated excess reagents from the first step and generated the stable N,O-acetal 43, which was a good acyliminium precursor
    • (b) The addition of methanol after the scission step was necessary to obtain good yields. If the fragmentation was followed by addition of the nucleophile and the Lewis acid, a complex product mixture was formed. The addition of methanol probably deactivated excess reagents from the first step and generated the stable N,O-acetal 43, which was a good acyliminium precursor.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.