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Volumn 65, Issue 27, 2009, Pages 5174-5180

A straightforward route to enantiopure α-substituted derivatives of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid

Author keywords

Alkylation; Bicyclic proline analogue; Perhydroindole 2 carboxylic acid; Quaternary amino acid

Indexed keywords

CARBON; CARBOXYLIC ACID DERIVATIVE; OCTAHYDROINDOLE 2 CARBOXYLIC ACID; PEPTIDE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 66149110786     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.006     Document Type: Article
Times cited : (10)

References (47)
  • 14
    • 66149152891 scopus 로고    scopus 로고
    • note
    • Hereafter, nomenclature without numerical locants at the stereochemical descriptors will be adopted for the sake of simplicity.
  • 20
    • 66149115844 scopus 로고    scopus 로고
    • U.S. Patent 20050106690
    • Hirata, N. U.S. Patent 20050106690, 2005;
    • (2005)
    • Hirata, N.1
  • 28
    • 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
  • 36
    • 0032962277 scopus 로고    scopus 로고
    • Seebach's self-reproduction of chirality methodology formally allows the direct α-alkylation of l-proline, with complete retention of configuration, through the formation of an intermediate oxazolidinone
    • Wang H., and Germanas J.P. Synlett (1999) 33-36 Seebach's self-reproduction of chirality methodology formally allows the direct α-alkylation of l-proline, with complete retention of configuration, through the formation of an intermediate oxazolidinone
    • (1999) Synlett , pp. 33-36
    • Wang, H.1    Germanas, J.P.2
  • 37
    • 66149134281 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the crude mixtures of the N-Boc protected amino esters (S,S,S)/(R,S,S)-5a-c were complex and unsuitable for the determination of the diastereomeric ratios due to the presence of conformational rotamers.
  • 38
    • 66149131282 scopus 로고    scopus 로고
    • note
    • Although the relative spatial disposition of substituents at the α carbon is identical for all three tetrasubstituted compounds (R,S,S)-6a, (R,S,S)-6b and (S,S,S)-6c, the stereochemical descriptors R/S giving the absolute configuration of the α carbon centre differ. This is due to the different priority of the substituents in the benzylated derivative in comparison with the methylated and allylated compounds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.