Palladium(0)-catalyzed regioselective synthesis of α-dehydro-β-amino esters from amines and allyl acetates: Synthesis of a α-dehydro-β-amino acid derived cyclic peptide as a constrained β-turn mimic

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7852-7857

  Rajesh, S ^a   Banerji, Biswadip ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY;

AMINES; CATALYSIS; HYDROGEN BONDS; ISOMERS; PALLADIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TEMPERATURE CONTROL;

ESTERS;

ALLYL COMPOUND; AMINE; BETA AMINO ACID; COBALT CHLORIDE; ESTER DERIVATIVE; HYDROGEN; PALLADIUM COMPLEX;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CYCLIZATION; HYDROGEN BOND; METAL BINDING; MOLECULAR DYNAMICS; MOLECULAR MIMICRY; PEPTIDE ANALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE MEASUREMENT;

ACETATES; AMINATION; AMINES; AMINO ACIDS; CATALYSIS; ESTERS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PALLADIUM; PEPTIDES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE;

EID: 0036828076     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo010981d     Document Type: Article

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47. For β-turn, see: (a) Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55. (b) Ball, J. B.; Hughes, R. A.; Alewood, P. L.; Andrews, P. R. Tetrahedron 1993, 49, 3467 and references therein. (c) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Turns in peptides and proteins. In Advances in Protein Chemistry; Academic Press: New York, 1985. (d) Farmer, P. S. In Drug Design; Ariens, E. J., Ed.; Academic: New York, 1980; Vol. 10, pp 119-143. (e) Feng, Y.; Pattarawarapan, M.; Wang, Z.; Burgess, K. Org. Lett. 1999, 1, 121. (f) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 2563-2569. (g) Kaul, R.; Angeles, A. R.; Jager, M.; Powers, E. T.; Kelly, J. J. Am. Chem. Soc, 2001, 123, 5206-5212.