메뉴 건너뛰기




Volumn 2, Issue 24, 2000, Pages 3883-3885

Memory of Chirality in Diastereoselective α-alkylation of Isoleucine and allo-isoleucine Derivatives

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ISOLEUCINE;

EID: 0034736318     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0066274     Document Type: Article
Times cited : (44)

References (28)
  • 10
    • 0033531681 scopus 로고    scopus 로고
    • Recently, excellent catalytic methods for asymmetric synthesis of α,α-disubstituted-α-amino acid derivatives have been developed, see: (a) Kuwano, R. Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3236
    • Kuwano, R.1    Ito, Y.2
  • 15
    • 84985560897 scopus 로고
    • For related asymmetric α-substitution of α-amino acid derivatives without using external chiral sources, see: (a) Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 971.
    • (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 971
    • Seebach, D.1    Wasmuth, D.2
  • 18
    • 0042490180 scopus 로고    scopus 로고
    • note
    • Chiral properties of A are time- and temperature-dependent. Therefore we call this type of chirality "dynamic chirality". Half-life to racemization of A is 22 h at -78°C: see ref 4c.
  • 24
    • 0042490179 scopus 로고    scopus 로고
    • note
    • 3:acetone = 60:1), giving a mixture of 7 and 8 (94% yield). Recrystallization from ether-hexane gave diastereomerically and analytically pure 7.
  • 26
    • 85086351986 scopus 로고    scopus 로고
    • note
    • -1, R = 0.052.
  • 27
    • 0041989289 scopus 로고    scopus 로고
    • note
    • The stereochemistry of 11 and 12 was determined after their conversion to 7 and 8.
  • 28
    • 0041989290 scopus 로고    scopus 로고
    • note
    • Enolate E is not axially chiral along the C(2)-N axis even if the bond rotation is restricted at -78°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.