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Volumn 39, Issue 21, 1998, Pages 3405-3408

Palladium-catalyzed formation and stereoselecttve isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 3 HYDROXY 5 PHENYLVALERIC ACID; OXAZOLIDINE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

EID: 0032555006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00534-6     Document Type: Article
Times cited : (36)

References (31)
  • 1
    • 0000182592 scopus 로고
    • Academic Press, Morrison, J. D. Ed, Orlando
    • For recent reviews see: (a) Lutomski, K. A.; Meyers, A. I. Asymmetric Synthesis, Academic Press, Morrison, J. D. Ed, Orlando, 1984, 3, 213.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 213
    • Lutomski, K.A.1    Meyers, A.I.2
  • 14
    • 0025253561 scopus 로고
    • Anti-selective allylation has been reported with one example giving 20.6:1: (a) Vara Prasad, J. V. N.; Rich, D. H. Tetrahedron Lett. 1990, 31, 1803. Syn-selective vinylation with 2-trimethylsilylethylidenetriphenylphosphorane gave excellent selectivites:
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1803
    • Vara Prasad, J.V.N.1    Rich, D.H.2
  • 15
    • 0026005194 scopus 로고
    • (b) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. Tandem DIBAL reduction of aminoesters and in-situ addition of vinyl nucleophiles has led to improved selectivity:
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6783
    • Franciotti, M.1    Mann, A.2    Taddei, M.3
  • 19
    • 22844434551 scopus 로고    scopus 로고
    • note
    • 3N
  • 20
    • 22844450195 scopus 로고    scopus 로고
    • note
    • 13C NMR and IR Spectroscopy.
  • 22
    • 22844434124 scopus 로고    scopus 로고
    • note
    • 3N
  • 23
    • 22844440086 scopus 로고
    • The cyclization of amides onto double bonds activated by sulphenylation has been limited to aryl amides as alkyl amides gave low (10%) yields. See ref 3a and Abd El Samii, Z. K. M.; Al Ashmay, M. I.; Mellor, J. M. Tetrahedron Lett. 1987, 28, 1929.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 1929
    • Abd El Samii, Z.K.M.1    Al Ashmay, M.I.2    Mellor, J.M.3
  • 24
    • 22844451274 scopus 로고    scopus 로고
    • note
    • AB INITIO calculations (Spartan) for the alanine derived oxazoline gave trans:cis ratios of 5.7:1 (STO-3G) and 6.7:1 (630G).
  • 25
    • 0000674932 scopus 로고
    • Palladium π-allyl complexes are known to undergo inversion. For mechanistic discussions, see: (a) Bäckvall, J.-E.; Granberg, K. L. J. Am. Chem. Soc. 1992, 114, 6858.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6858
    • Bäckvall, J.-E.1    Granberg, K.L.2
  • 27
    • 22844447747 scopus 로고    scopus 로고
    • note
    • Good diastereoselectivity with serinal derivatives has been particularly problematic. See refs. 5b and 5c.
  • 28
    • 0025250109 scopus 로고
    • 1H NMR chemical shifts of the ring protons (0.3 to 0.5 ppm upfield shift for trans relative to cis) in analogy to the reported oxazolidinones. Sakaitani, M.; Ohfune, Y. J. Am. Chem. Soc. 1990, 112, 1150.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 1150
    • Sakaitani, M.1    Ohfune, Y.2
  • 30
    • 0001172518 scopus 로고
    • Barrett, A. J.; Savesen, G. eds, Elsevier, New York
    • (b) Rich, D. H. in "Proteinase Inhibitors," Barrett, A. J.; Savesen, G. eds, Elsevier, New York, 1986, p. 179.
    • (1986) Proteinase Inhibitors , pp. 179
    • Rich, D.H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.