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Volumn 128, Issue 17, 2006, Pages 5600-5601

Enantioselective, facially selective carbomagnesation of cyclopropenes

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYMETHYLCYCLOPROPENE; ACETAL; ACETYLENE; ALKENE; CARBOXYLIC ACID; COPPER; CYCLOPROPENE; DIAZONIUM COMPOUND; GRIGNARD REAGENT; MAGNESIUM; METHANOL; REAGENT; UNCLASSIFIED DRUG;

EID: 33646577802     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058101q     Document Type: Article
Times cited : (86)

References (37)
  • 7
    • 33646597313 scopus 로고    scopus 로고
    • note
    • Preparations of 1 were based on footnote 9a and references therein.
  • 28
    • 0003491440 scopus 로고    scopus 로고
    • de Meijere, Ed.; Georg Thieme Verlag: Stuttgart
    • (d) Methoden der Organischen Chemie (Houben Weyl): de Meijere, Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol E17a.
    • (1996) Methoden der Organischen Chemie (Houben Weyl) , vol.E17A
  • 29
    • 33646586118 scopus 로고    scopus 로고
    • note
    • 2a but not for 1a. The likely explanation for the lower reactivity of the former (without Cu) is that alkyl substitution considerably increases the strength of the cyclopropane C=C bond. See ref 5a.
  • 31
    • 0345711474 scopus 로고    scopus 로고
    • For examples of alkoxide-promoted enantioselective reactions of dialkylzinc and organolithium reagents, see: (b) Vogl, E. M.; Gröger, G.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1570
    • Vogl, E.M.1    Gröger, G.2    Shibasaki, M.3
  • 35
    • 33646590665 scopus 로고    scopus 로고
    • note
    • The adduct from 3-hydroxymethyl-3-phenylcydopropene gave the lactol in 98% ee after DMF quench (Table 1). Also observed was < 10% of 2 in 50% ee. The low ee for 2 is consistent with enantiomeric enrichment via kinetic resolution.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.