Chiral N-phosphonyl imine chemistry: Asymmetric additions of ester enolates for the synthesis of β-amino acids

Chemical Biology and Drug Design

Volumn 72, Issue 2, 2008, Pages 120-126

  Han, Jianlin ^a   Ai, Teng ^a   Nguyen, Thao ^a   Li, Guigen ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

amino acid; Chiral N phosphonyl imines; Chiral phosphoramide; Lithium enolate; Triisopropoxytitanium(IV) chloride

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID; ESTER DERIVATIVE; HYDROBROMIC ACID; IMINE; LEWIS ACID; LITHIUM DERIVATIVE; N PHOSPHONYLIMINE; NAPHTHYL GROUP; PHOSPHONIC ACID DERIVATIVE; TITANIUM DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ISOMERISM; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

AMINO ACIDS; ESTERS; IMINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOSPHORUS; SOLVENTS; STEREOISOMERISM;

EID: 47949118819     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00682.x     Document Type: Article

References (40)

1. Lelais G., Seebach D. (2004) Beta (2)-amino acids - syntheses, occurrence in natural products, and components of beta-peptides. Biopolymers 76 : 206 243.
2. Lee M.-R., Raguse T.L., Schinerl M., Pomerantz W.C., Wang X., Wipf P., Gellman S.H. (2007) Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in peptides. Org Lett 9 : 1801 1804.
3. Liu M., Sibi M.P. (2002) Recent advances in the stereoselective synthesis of beta-amino acids. Tetrahedron 58 : 7991 8035.
4. Hayashi Y., Katada J., Harada T., Tachiki A., Iijima K., Takiguchi Y., Muramatsu M., Miyazaki H., Asari T., Okazaki T., Sato Y., Yasuda E., Yano M., Uno I., Ojima I. (1998) GPIIb/IIIa integrin antagonists with the new conformational restriction unit, trisubstituted β-amino acid derivatives, and a substituted benzamidine structure. J Med Chem 41 : 2345 2360.
5. Iijima K., Katada J., Hayashi Y. (1999) Symmetrical anhydride-type serine protease inhibitors: Structure-activity relationship studies of human chymase inhibitors. Bioorg Med Chem Lett 9 : 413 418.
6. Bai R.L., Verdier-Pinard P., Gangwar S., Stessman C.C., McClure K.J., Sausville E.A., Pettit G.R., Bates R.B., Hamel E. (2001) Dolastatin 11, a marine depsipeptide, arrests cells at cytokinesis and induces hyperpolymerization of purified actin. Mol Pharmacol 59 : 462 469.
7. Bates R.B., Brusoe K.G., Burns J.J., Caldera S., Cui W., Gangwar S., Gramme M.R., McClure K.J., Rouen G.P., Schadow H., Stessman C.C., Taylor S.R., Vu V.H., Yarick G.V., Zhang J.X., Pettit G.R., Bontems R. (1997) Dolastatins 26. Synthesis and stereochemistry of dolastatin 11. J Am Chem Soc 119 : 2111 2113.
8. Jefferson E.A., Swayze E.E. (1999) β-Amino acid facilitates macrocyclic ring closure in a combinatorial library. Tetrahedron Lett 40 : 7757 7760.
9. Kaseda T., Kikuchi T., Kibayashi C. (1989) Enantioselective total synthesis of (+)-(S)-dihydroperiphylline. Tetrahedron Lett 30 : 4539 4542.
10. Enders D., Moser M., Geibel G., Laufer M.C. (2004) Diastereo- and enantioselective synthesis of differently N,O-protected 1,3-amino alcohols with three neighbouring stereogenic centers. Synthesis 2004 : 2040 2046 references cited therein.
11. Kochi T., Tang T.P., Ellman J.A. (2003) Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols. J Am Chem Soc 125 : 11276 11282.
12. Wenzel A.G., Jacobsen E.N. (2005) Enantioselective Synthesis of β-Amino Acids, 2nd edn. MA : John Wiley & Sons.
13. Juaristi E. (1997) Enantioselective Synthesis of β-Amino Acids, 1st edn. New York : Wiley-VCH.
14. Chi Y., English E.P., Pomerantz W.C., Horne W., Seth J., Leo A., Alexander L.R., Fleming W.S., Hopkins E.A., Gellman S.H. (2007) Practical synthesis of enatiomerically pure 2-amino acids via proline-catalyzed diastereoselective aminomethylation of aldehydes. J Am Chem Soc 129 : 6050 6055.
15. Juaristi E., Quintana D., Balderas M., Garcial P.E. (1996) Enantioselective synthesis of beta-amino acids.7. Preparation of enantiopure alpha-substituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3- methylperhydropyrimidin-4-one. Tetrahedron Asymmetry 7 : 2233 2246.
16. 2-amino acids. J Am Chem Soc 128 : 6804 6805.
17. Hsiao Y., Rivera N.R., Rosner T. (2004) Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines. J Am Chem Soc 126 : 9918 9919.
18. Sibi M.P., Itoh K. (2007) Organocatalysis in conjugate amine additions. Synthesis of β-amino acid derivatives. J Am Chem Soc 129 : 8064 8065.
19. Sibi M.P., Prabagaran N., Ghorpade S.G., Jasperse C.P. (2003) Enantioselective synthesis of α,β-disubstituted-β-amino acids. J Am Chem Soc 125 : 11796 11797.
20. Sibi M.P., Shay J.J., Liu M., Jasperse C.P. (1998) Chiral Lewis acid catalysis in conjugate additions of O-benzylhydroxylamine to unsaturated amides. Enantioselective synthesis of β-amino acid precursors. J Am Chem Soc 120 : 6615 6616.
21. Myers J.K., Jacobsen E.N. (1999) Asymmetric synthesis of β-amino acid derivatives via catalytic conjugate addition of hydrazoic acid to unsaturated imides. J Am Chem Soc 121 : 8959 8960.
22. Zhu G., Chen Z., Zhang X. (1999) Highly efficient asymmetric synthesis of β-amino acid derivatives via rhodium-catalyzed hydrogenation of β-(acylamino)acrylates. J Org Chem 64 : 6907 6910.
23. 2-amino acid derivatives. Tetrahedron: Asymmetry 16 : 1309 1319.
24. Miyabe H., Fujii K., Naito T. (2003) Radical addition to oxime ethers for asymmetric synthesis of β-amino acid derivatives. Org Biomol Chem 1 : 381 390.
25. 2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives. Org Biomol Chem 5 : 2812 2825.
26. Allef P., Kunz H. (2000) Glycosylation-induced asymmetric synthesis: β-amino acid esters via Mannich reactions. Tetrahedron: Asymmetry 11 : 375 378.
27. Tillman A.L., Ye J., Dixon D.J. (2006) Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative. Chem Commun 2006 : 1191 1193.
28. Kise N., Ueda N. (1999) A new method for the synthesis of β-amino acid derivatives and β-lactams. Reaction of N-alkoxycarbonyl-1- methoxyamines with esters. J Org Chem 64 : 7511 7514.
29. Cainelli G., Panunzio M., Bandini E., Martelli G., Spunta G. (1996) Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans-azetidin-2-ones in high stereocontrolled fashion. Tetrahedron 52 : 1685 1698.
30. Cozzi P.G., Simone B.D., Umani-Ronchi A. (1996) Highly diastereoselective addition of silyl enolates to chiral imines derived from (S)-valine methyl ester using lanthanide triflate. Tetrahedron Lett 37 : 1691 1694.
31. 6arene)chromium(0) complexes as chiral auxiliaries: asymmetric synthesis of β-aminoesters and β-lactams by Reformatsky condensation. Tetrahedron 52 : 4849 4856.
32. Tang T.P., Ellman J.A. (2002) Asymmetric synthesis of β-amino acid derivatives incorporating a broad range of substitution patterns by enolate additions to tert-butanesulfinyl imines. J Org Chem 67 : 7819 7832.
33. Tang T.P., Ellman J.A. (1999) The tert-butanesulfinyl Group: an ideal chiral directing group and Boc-surrogate for the asymmetric synthesis and applications of β-amino acids. J Org Chem 64 : 12 13.
34. Davis F.A., Reddy R.E., Szewczyk J.M. (1995) Asymmetric synthesis of (R)-(+)-beta.-Phenylalanine from (S)-(+)-benzylidene-p-toluenesulfinamide. Regeneration of the sulfinimine precursor. J Org Chem 60 : 7037 7039.
35. Fujisawa T., Kooriyama Y., Shimizu M. (1996) Switchover of diastereofacial selectivity in the condensation reaction of optically active N-sulfinimine with ester enolate. Tetrahedron Lett 37 : 3881 3884.
36. Kattuboina A., Li G. (2008) Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions. Tetrahedron Lett 49 : 1573 1577.
37. Kattuboina A., Kaur P., Ai T., Li G. (2008) Asymmetric Aza-Henry reaction using chiral N-phosphonyl imines. Chem Biol and Drug Des 71 : 216 223.
38. Han J.L., Ai T., Li G. (2008) Chiral N-phosphonylimine chemistry: asymmetric addition of betone-derived enolates for the synthesis of β-amino ketones. Synthesis In press.
39. Siegel C., Thornton E.R. (1989) Asymmetric aldol reactions. A titanium enolate giving very high diastereofacial selectivities. J Am Chem Soc 111 : 5722 5728.
40. Crombie L., Haigh D., Jones R.C.F., Mat-Zin A.R. (1993) Synthesis of the alkaloid homaline in (±) and natural (S,S)-(-) forms, using amination and transamidative ring expansion in liquid ammonia. J Chem Soc, Perkin Trans 1 1993 : 2047 2054.