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Volumn 61, Issue 27, 2005, Pages 6546-6552

Concise and diastereoselective approach to syn- and anti-N-tosyl-α- hydroxy β-amino acid derivatives

Author keywords

Diazo carbonyl compounds; Amino acid; Imine; Regioselective reduction

Indexed keywords

ACETIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; ESTER DERIVATIVE; IMINE; N TOSYL ALPHA HYDROXY BETA AMINO ACID DERIVATIVE; SODIUM PEROXIDE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 20444482899     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.054     Document Type: Article
Times cited : (24)

References (35)
  • 5
    • 0028130028 scopus 로고
    • For reviews on β-amino acid synthesis, see: (a) D.C. Cole Tetrahedron 50 1994 9517 9582
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 12
    • 0002292746 scopus 로고    scopus 로고
    • For review on the synthesis of α-hydroxy-β-amino acids in particular, see: (h) R. Andruszkiewicz Polish J. Chem. 72 1998 1 28
    • (1998) Polish J. Chem. , vol.72 , pp. 1-28
    • Andruszkiewicz, R.1
  • 25
    • 20444496689 scopus 로고    scopus 로고
    • note
    • For α-oxo ester 6c, both reduction and hydrogenation gave diminished stereoselectivities (Table 2, entry 3). We speculate that the product 4c and 5c may epimerize under the reaction and workup conditions.
  • 26
    • 20444500334 scopus 로고    scopus 로고
    • note
    • The authors have deposited the refined coordinates for 4c with the Cambridge Crystallographic Data Centre (deposition number 235122). Copies of the available material can be obtained free of charge on application to the CCDC, 12, Union Road, Cambridge, CB2 1EZ, UK Email: deposit@ccdc.cam.ac.uk.
  • 33
    • 0035844659 scopus 로고    scopus 로고
    • For the examples of other approaches leading to both syn- and anti-α-hydroxyl β-amino acid derivatives, see: (a) T. Akiyama, J. Takaya, and H. Kagoshima Tetrahedron Lett. 42 2001 4025 4028
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4025-4028
    • Akiyama, T.1    Takaya, J.2    Kagoshima, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.