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Volumn 56, Issue 24, 2000, Pages 3951-3961

Et3B- and et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions

Author keywords

Glyoxylate imines; Radical additions; Triethylborane diethylzinc

Indexed keywords

GLYOXYLIC ACID DERIVATIVE; IMINE; OXAZINE DERIVATIVE; RADICAL;

EID: 0034625430     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00327-6     Document Type: Article
Times cited : (94)

References (67)
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    • For the synthesis of alcohols see: (c) Abraham, M. H. J. Chem. Soc. 1960, 4130-4135.
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  • 39
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    • note
    • · was overwhelming compared to the addition of the corresponding primary alkyl radical. The reaction is limited to secondary and tertiary alkyl iodides.
  • 43
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    • note
    • · were also isolated in 10% yield (3d:4d, 23:77).
  • 50
    • 84992625568 scopus 로고    scopus 로고
    • note
    • A competitive experiment was carried out on an equimolar mixture of 1a and 2b under conditions (i) at -40°C in the presence of 6 equiv. of t-BuI. Approximately 50% of unreacted 1a was recovered, together with 7a and 8a, and 2b was completely transformed into a mixture of 12, 13 and 16, 17.
  • 59
    • 84992642138 scopus 로고    scopus 로고
    • note
    • In the case of 1b, the structure of which is very close to that of 1a, the assignments were based on the relative shielding of the proton α to the amino group and to the carboxylate in the diastereomeric products. With regard to 1c and 1d, correlations can be established between the relative chemical shift of the proton α to nitrogen in the chiral auxiliary in the diastereomeric adducts and their sterochemistry. Similar trends are observed in literature data, see Refs. 16f-h.
  • 60
    • 84992642137 scopus 로고    scopus 로고
    • note
    • 2; the injection of 20 mL of air corresponds approximately to 35 or 20% molar quantities of oxygen.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.