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Volumn 13, Issue 6, 2002, Pages 563-567

Use of α-amino esters as chiral auxiliaries in the enantioselective Michael alkylation of chiral imines

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLGLYCINE METHYL ESTER; ALKENE DERIVATIVE; ALPHA METHYLBENZYLAMINE; ASPARTIC ACID DIMETHYL ESTER; ESTER DERIVATIVE; IMINE; UNCLASSIFIED DRUG; VALINE ESTER;

EID: 0037134291     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00171-4     Document Type: Article
Times cited : (14)

References (37)
  • 28
    • 0008910736 scopus 로고    scopus 로고
    • α-Amino esters were obtained by treatment of their corresponding commercial hydrochloride salt with aqueous NaOH solution (1 M) and subsequent extraction with dichloromethane.
  • 29
    • 0008930798 scopus 로고    scopus 로고
    • Chiral imines 1a-d were obtained from the corresponding amines and 2-methylcyclohexanone (1 equiv.) in refluxing toluene in a Dean-Stark water separator for 24 h.
  • 31
    • 0008890450 scopus 로고    scopus 로고
    • Such a method for determination of the diastereoselectivity has already been used in similar cases: see Ref. 2.
  • 32
    • 0008960962 scopus 로고    scopus 로고
    • Crude chiral imines 1a-d were reacted under an argon atmosphere with phenyl acrylate (1.1 equiv.) at rt for 3 h and the reaction mixture was then heated at 100°C for 4 days. The reaction medium was then analyzed by GC-MS affording the de values displayed in Table 1. After dissolution in ether and basic aqueous washing (NaOH 1 M) the residue was purified by flash chromatography (EtOAc/cyclohexane) on silica gel.
  • 33
    • 0008960963 scopus 로고    scopus 로고
    • note
  • 34
    • 0008948357 scopus 로고    scopus 로고
    • The same procedure as described for phenyl acrylate (Ref. 11) was used with imine 1b.
  • 35
    • 0008937250 scopus 로고    scopus 로고
    • These two olefins were prepared according to Ref. 1f.
  • 36
    • 0008953021 scopus 로고    scopus 로고
    • Lactams 6a and 8a were obtained as an isomeric mixture of compounds differing in their double bond position (Ref. 1f) while 9 could be separated in the present instance.
  • 37
    • 0008890451 scopus 로고    scopus 로고
    • note


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.