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Volumn , Issue 2, 2009, Pages 213-216

Asymmetric pentenylation of aldehydes: A new benchmark for the preparation of ethyl-substituted homoallylic alcohol

Author keywords

, unsaturated lactone; Asymmetric pentenylation; Ring closing metathesis

Indexed keywords


EID: 62349089357     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087641     Document Type: Article
Times cited : (11)

References (35)
  • 1
    • 0346908681 scopus 로고    scopus 로고
    • For recent reviews, see: a, Yamamoto, H, Oshima, K, Eds, Wiley-VCH: Weinheim
    • For recent reviews, see: (a) Main Group Metals in Organic Synthesis, Vol. 2; Yamamoto, H.; Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004.
    • (2004) Main Group Metals in Organic Synthesis , vol.2
  • 7
    • 0002446724 scopus 로고
    • Trost, B. M, Fleming, I, Heathcock, C. H, Eds, Pergamon: Oxford
    • (g) Roush, W. R. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, 1991, 1-53.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1-53
    • Roush, W.R.1
  • 11
    • 0001197542 scopus 로고
    • A racemic pentenylation of aldehydes was developed by Fujita and Schlosser. See
    • A racemic pentenylation of aldehydes was developed by Fujita and Schlosser. See: Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258.
    • (1982) Helv. Chim. Acta , vol.65 , pp. 1258
    • Fujita, K.1    Schlosser, M.2
  • 23
    • 62349131044 scopus 로고    scopus 로고
    • It is noteworthy that optically active ethyl-substituted homoallylic alcohols are exclusively accessed through aldol chemistry
    • It is noteworthy that optically active ethyl-substituted homoallylic alcohols are exclusively accessed through aldol chemistry.
  • 24
    • 62349135118 scopus 로고    scopus 로고
    • General Procedure for the syn-Selective Boron-Mediated Pentenylation Reaction: To a stirred suspension of t-BuOK (1.1 equiv) and (Z)-2-pentene (2.2 equiv) in THF at -78°C was added n-BuLi (1.1 equiv) dropwise. After complete addition, the reaction mixture was stirred for 5 min at -50°C. The resulting orange solution was then cooled to -78°C and to it, was added dropwise a solution of, )-methoxydiisopinocampheylborane in Et2O (1.35 equiv, 0.5 M in Et2O, After stirring for 30 min at -78°C, boron trifluoride diethyl etherate (1.5 equiv) was added followed by the aldehyde 1 equiv, The reaction mixture was then stirred for an extra 5 h at the same temperature before it was treated with a 3 M solution of NaOH and H2O2 and refluxed for 1 h. The reaction mixture was then extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crud
    • 4 and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel using a gradient of eluents to afford the corresponding homoallylic alcohol.
  • 25
    • 62349099596 scopus 로고    scopus 로고
    • Since the (Z)-crotyl potassium species are thermodynamically more stable than the corresponding E-isomer, preferential access to syn-substituted homoallylic alcohols is observed with them. See: (a) Schlosser, A.; Despond, O.; Lehmann, R.; Moret, E.; Rauchschwalbe, G. Tetrahedron 1993, 49, 10175.
    • Since the (Z)-crotyl potassium species are thermodynamically more stable than the corresponding E-isomer, preferential access to syn-substituted homoallylic alcohols is observed with them. See: (a) Schlosser, A.; Despond, O.; Lehmann, R.; Moret, E.; Rauchschwalbe, G. Tetrahedron 1993, 49, 10175.
  • 29
    • 62349134819 scopus 로고    scopus 로고
    • Same procedure as previously employed except that the temperature was not raised to -50°C after the addition of n-BuLi.
    • Same procedure as previously employed except that the temperature was not raised to -50°C after the addition of n-BuLi.
  • 34
    • 0000487061 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (a) Heathcock, C. H. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 181.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 181
    • Heathcock, C.H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.