메뉴 건너뛰기




Volumn 64, Issue 1, 2008, Pages 84-91

Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid

Author keywords

Alkylation; Bicyclic proline analogue; Crystal structure; Perhydroindole 2 carboxylic acid; Quaternary amino acid; Self reproduction of chirality; Trichloromethyloxazolidinone

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; OCTAHYDROINDOLE 2 CARBOXYLIC ACID; OXAZOLIDINONE DERIVATIVE; PROLINE DERIVATIVE; TRICHLOROMETHYLOXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 36348968945     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.095     Document Type: Article
Times cited : (19)

References (38)
  • 5
    • 84989315628 scopus 로고    scopus 로고
    • Substituted Prolines: Syntheses and Applications in Structure-Activity Relationship Studies of Biologically Active Peptides
    • Attanasi O.A., and Spinelli D. (Eds), Royal Society of Chemistry, Cambridge
    • Karoyan P., Sagan S., Lequin O., Quancard J., Lavielle S., and Chassaing G. Substituted Prolines: Syntheses and Applications in Structure-Activity Relationship Studies of Biologically Active Peptides. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems: Chemistry and Properties Vol. 8 (2005), Royal Society of Chemistry, Cambridge 216-273
    • (2005) Targets in Heterocyclic Systems: Chemistry and Properties , vol.8 , pp. 216-273
    • Karoyan, P.1    Sagan, S.2    Lequin, O.3    Quancard, J.4    Lavielle, S.5    Chassaing, G.6
  • 17
    • 36349001308 scopus 로고    scopus 로고
    • Barvian, N. C.; Connolly, C. J. C.; Guzzo, P. R.; Hamby, J. M.; Hicks, J. L.; Johnson, M. R.; Le, V.-D.; Mitchell, L. H.; Roark, W. H. PCT Patent WO 2004092132, 2004.
  • 23
    • 36348972477 scopus 로고    scopus 로고
    • Hirata, N. U.S. Patent 0,106,690, 2005.
  • 30
    • 36348940587 scopus 로고    scopus 로고
    • note
    • Note that the order of stereochemical descriptors R/S obey different numeration profiles in compounds 1 and 2. In particular, the α carbon occupies position 2 in the former and position 9a in the latter. Abbreviated names, with and without numerical locants, are exemplified below for clarity. {A figure is presented}
  • 32
    • 36348962568 scopus 로고    scopus 로고
    • note
    • The preparation of trichloromethyloxazolidinones was preferred to tert-butyloxazolidinones because of their greater stability. In the case of proline, the corresponding trichloromethyloxazolidinone is a crystalline solid, while the tert-butyl derivative is highly sensitive to hydrolysis and unstable in air.
  • 33
    • 36348981746 scopus 로고    scopus 로고
    • note
    • Unreacted (S,S,S)-1 can be isolated, if desired, by washing the silica pad with MeOH.
  • 36
    • 36348973626 scopus 로고    scopus 로고
    • note
    • Although the relative spatial disposition of substituents at carbon 9a is identical for all three tetrasubstituted compounds 3a-c, the stereochemical descriptors R/S giving the absolute configuration of the carbon centre differ. Thus, the compound with a benzyl substituent (3b) has an S configuration at position 9a due to the different priority of the substituents in comparison with the methyl or allyl derivatives.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.