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Volumn 128, Issue 47, 2006, Pages 15215-15220

Enantioselective synthesis of diversely substituted quaternary 1,4-benzodiazepin-2-ones and 1,4-benzodiazepine-2,5-diones

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; AMINO ACIDS; BIOMEDICAL ENGINEERING; CONFORMATIONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 33845211978     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0640142     Document Type: Article
Times cited : (51)

References (38)
  • 10
    • 0345022255 scopus 로고
    • The term chirality in the phrase "memory of chirality" originally coined by Fuji (Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694-9696) properly refers to the sense of chirality, or configuration. Chirality is retained in the intermediates whether they racemize or remain enantiopure; the same is obviously true of the products. Perhaps a better term would be "memory of configuration".
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9694-9696
    • Kawabata, T.1    Yahiro, K.2    Fuji, K.3
  • 24
    • 33845229256 scopus 로고    scopus 로고
    • note
    • The chloro substituent in these 1,4-benzodiazepin-2-ones derives from the 2-amino-5-chlorobenzophenone starting material, a commercially available intermediate used in the production of diazepam.
  • 25
    • 33845209306 scopus 로고    scopus 로고
    • note
    • One possible explanation for the need for excess base is that alkylation occurs more quickly on a KHMDS/potassium enolate mixed aggregate than it does on homomeric potassium enolates.
  • 28
    • 0018636458 scopus 로고
    • This dihedral angle has the same sign as the C2-C3-N4-C5 dihedral, which has historically (Konowal, A.; Snatzke, G.; Alebic-Kolbah, T.; Kajfez, F.; Rendic, S.; Sunjic, V. Biochem. Pharm. 1979, 28, 3109-3113) been used to designate the sense of conformational chirality of the benzodiazepine ring.
    • (1979) Biochem. Pharm. , vol.28 , pp. 3109-3113
    • Konowal, A.1    Snatzke, G.2    Alebic-Kolbah, T.3    Kajfez, F.4    Rendic, S.5    Sunjic, V.6
  • 38
    • 33845204497 scopus 로고    scopus 로고
    • unpublished work
    • Consistent with this analysis, preliminary deprotonation/trapping studies of N-i-Pr-1,4-benzodiazepin-2-one (S)-1d indicate the potassium enolate has a racemization barrier of 18 kcal/mol (258 K). In contrast, the same technique indicates only a 12.5 kcal/mol barrier (173 K) for the potassium enolate derived from N-i-Pr-1,4-benzodiazepine-2,5-dione (S)-3d (P. C.-H. Lam, S. L. MacQuarrie-Hunter, and P. R. Carlier, unpublished work).
    • Lam, P.C.-H.1    MacQuarrie-Hunter, S.L.2    Carlier, P.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.