메뉴 건너뛰기




Volumn 1, Issue 21, 2003, Pages 3708-3715

Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acid

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINATION; HYDROLYSIS; HYDROXYLATION; ISOMERS; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0344118919     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b306936m     Document Type: Article
Times cited : (50)

References (65)
  • 45
    • 0345483767 scopus 로고    scopus 로고
    • For a review of electrophilic amination procedures see: C. Greck and J. P. Genet, Synlett, 1997, 741.
    • (1997) Synlett , pp. 741
    • Greck, C.1    Genet, J.P.2
  • 48
    • 0030021962 scopus 로고    scopus 로고
    • note
    • This observation is in accord with that of Heimgartner and coworkers who shwoed that when the lithium enolates derived from N-methyl-N-phenylcarboxamides were treated with diphenyl-phosphoryl azide at 0 °C the corresponding α-diazoamide was obtained as the sole reaction product, see: J. M. Villalgordo, A. Linden and H. Heimgartner, Helv. Chim. Acta, 1996, 79, 213.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 213
    • Villalgordo, J.M.1    Linden, A.2    Heimgartner, H.3
  • 63
    • 0029074988 scopus 로고
    • Participation of a neighbouring N-Boc group and in situ oxazolidinone formation with either a triflate or tosylate leaving group have been reported, see: Y. Nakamura, M. Hirai, K. Tamotsu, Y. Yonezawa and C. Shin, Bull. Chim. Soc. Jpn, 1995, 68, 1369.
    • (1995) Bull. Chim. Soc. Jpn , vol.68 , pp. 1369
    • Nakamura, Y.1    Hirai, M.2    Tamotsu, K.3    Yonezawa, Y.4    Shin, C.5
  • 64
    • 84988742408 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the anti- and syn-diastereo-isomers 2 and 3 respectively showed distinct differences in coupling constans, with the C(2)-C(3) coupling constant in the syn-isomer being ∼3 Hz, while in the anti-diastereoisomer it is 7 Hz, consistent with those noted by Janda et al. (see reference 25).
  • 65
    • 84988766064 scopus 로고    scopus 로고
    • note
    • (2S,3S)-ter-Butyl 2-hydroxy-3-aminobutanoate 21 is commercially available from Evotec OAI.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.