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Volumn 12, Issue 12, 2010, Pages 2706-2709

Highly (E)-selective BF3·Et2O-promoted allylboration of chiral nonracemic α-Substituted allylboronates and analysis of the origin of stereocontrol

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALLYL COMPOUND; BORONIC ACID DERIVATIVE;

EID: 77953598605     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1007444     Document Type: Article
Times cited : (49)

References (117)
  • 9
    • 77953607549 scopus 로고    scopus 로고
    • For carbonyl addition with α-hetero atom substituted allylboronates
    • For carbonyl addition with α-hetero atom substituted allylboronates
  • 28
    • 77953550477 scopus 로고    scopus 로고
    • For carbonyl addition with α-alkyl-substituted allylboronates
    • For carbonyl addition with α-alkyl-substituted allylboronates
  • 34
    • 0022928221 scopus 로고
    • For synthetic applications
    • For synthetic applications: Ditrich, K.; Bube, T.; Stürmer, R.; Hoffmann, R. W. Angew. Chem., Int. Ed. 1986, 25, 1028
    • (1986) Angew. Chem., Int. Ed. , vol.25 , pp. 1028
    • Ditrich, K.1
  • 48
    • 77953570872 scopus 로고    scopus 로고
    • For recent development of α-substituted allylboronates
    • For recent development of α-substituted allylboronates
  • 82
    • 77953567159 scopus 로고    scopus 로고
    • For alternative approaches to δ-methyl-homoallylic alcohols
    • For alternative approaches to δ-methyl-homoallylic alcohols
  • 111
    • 69849114338 scopus 로고    scopus 로고
    • Syn -pentane interactions plays an important role in stereoselectivity
    • For recent examples where minimization of
    • For recent examples where minimization of syn -pentane interactions plays an important role in stereoselectivity: Liu, J.; De Brabander, J. K. J. Am. Chem. Soc. 2009, 131, 12562
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 12562
    • Liu, J.1    De Brabander, J.K.2
  • 116
    • 77953565197 scopus 로고    scopus 로고
    • note
    • Coordination to the non-bonded electron pair (indicated in red) is disfavored owing to a 1,3-interaction with the angular methyl group. Coordination to the distal oxygen atom is disfavored for steric reasons.
  • 117
    • 0141930412 scopus 로고
    • note
    • The enantiomeric purity of homoallylic alcohols 14 and 15 was ca.15-30% ee, presumably due to epimerization of the α-chloro center during preperations of reagents 13a and 13b. Matteson, D. S.; Erdik, E. Organmetallics 1983, 2, 1083
    • (1983) Organmetallics , vol.2 , pp. 1083
    • Matteson, D.S.1    Erdik, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.