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Volumn 134, Issue 17, 2012, Pages 7570-7574

Erratum: Synthesis of enantioenriched tertiary boronic esters from secondary allylic carbamates. Application to the synthesis of C30 botryococcene (Journal of the American Chemical Society (2012) 134 (7570-7575) DOI: 10.1021/ja303022d);Synthesis of enantioenriched tertiary boronic esters from secondary allylic carbamates. Application to the synthesis of C30 botryococcene

Author keywords

[No Author keywords available]

Indexed keywords

STEREOCHEMISTRY; STEREOSELECTIVITY;

EID: 84860791937     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304872j     Document Type: Erratum
Times cited : (78)

References (67)
  • 10
    • 0142174551 scopus 로고    scopus 로고
    • Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation
    • Hodgson, D. M. Springer: London
    • Hoppe, D.; Marr, F.; Brüggemann, M. Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation. Organolithiums in Enantioselective Synthesis; Hodgson, D. M., Ed.; Springer: London, 2003; Vol. 5, p 73.
    • (2003) Organolithiums in Enantioselective Synthesis , vol.5 , pp. 73
    • Hoppe, D.1    Marr, F.2    Brüggemann, M.3
  • 21
    • 84860830462 scopus 로고    scopus 로고
    • Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution
    • Dynamic kinetic resolution: Christmann, M. Bräse, S. Wiley-VCH: Weinheim
    • Dynamic kinetic resolution: Gais, H.-J. Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution. Asymmetric Synthesis-The Essentials; Christmann, M.; Bräse, S., Eds.; Wiley-VCH: Weinheim, 2006; pp 84-89.
    • (2006) Asymmetric Synthesis - The Essentials , pp. 84-89
    • Gais, H.-J.1
  • 22
    • 79957438896 scopus 로고    scopus 로고
    • Arylation and alkenylation of carbonyl and imino groups
    • Nucleophilic addition to aldehydes: De Vries, J. G. Molander, G. A. Evans, P. A. Georg Thieme Verlag: Stuttgart
    • Nucleophilic addition to aldehydes: Kauffman, M. C.; Walsh, P. J. Arylation and alkenylation of carbonyl and imino groups. Science of Synthesis, Stereoselective Synthesis; De Vries, J. G.; Molander, G. A.; Evans, P. A., Eds.; Georg Thieme Verlag: Stuttgart, 2011; Vol. 2, pp 449-495.
    • (2011) Science of Synthesis, Stereoselective Synthesis , vol.2 , pp. 449-495
    • Kauffman, M.C.1    Walsh, P.J.2
  • 24
    • 0002041453 scopus 로고    scopus 로고
    • Catalytic Asymmetric Epoxidation of Allylic Alcohols
    • Sharpless epoxidation resolution: 2 nd ed. Ojima, I. Wiley-VCH: New York
    • Sharpless epoxidation resolution: Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Epoxidation of Allylic Alcohols. In Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 231-280.
    • (2000) Catalytic Asymmetric Synthesis , pp. 231-280
    • Johnson, R.A.1    Sharpless, K.B.2
  • 25
    • 0037131143 scopus 로고    scopus 로고
    • 3 = Ph, homolytic cleavage of the C-B bond in 5 will produce two stabilized radicals, resulting in racemization of the γ -stereocenter. For radical oxidation of boronic esters, see: Cadot, C.; Dalko, P. I.; Cossy, J. J. Org. Chem. 2002, 67, 7193
    • (2002) J. Org. Chem. , vol.67 , pp. 7193
    • Cadot, C.1    Dalko, P.I.2    Cossy, J.3
  • 27
    • 34447542845 scopus 로고    scopus 로고
    • Deprotonation of 1f over 15 and 60 min, followed by trapping with boronic ester 2b, gave 4fb with 72:28 and 58:42 er respectively indicating that the lithiated carbamate was configurationally unstable at this temperature. The reasons for this are unclear but could be related to cyclohex-2-enyl carbamate that Hoppe has studied: Becker, J.; Fröhlich, R.; Salorinne, K.; Hoppe, D. Eur. J. Org. Chem. 2007, 3337
    • (2007) Eur. J. Org. Chem. , pp. 3337
    • Becker, J.1    Fröhlich, R.2    Salorinne, K.3    Hoppe, D.4
  • 28
    • 0026754759 scopus 로고
    • Both E and Z allyl carbamates 1a and 1g gave the same major enantiomer and double bond isomer tertiary alcohol 4ab upon lithiation-borylation. This was surprising, as Hoppe had found that stannylation of the same lithiated carbamates led to enantiomeric stannanes: Zschage, O.; Schwark, J.-R.; Krämer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377
    • (1992) Tetrahedron , vol.48 , pp. 8377
    • Zschage, O.1    Schwark, J.-R.2    Krämer, T.3    Hoppe, D.4
  • 32
    • 84860830460 scopus 로고    scopus 로고
    • Scientific American. Navy Green: Military Investigates Biofuels to Power Its Ships and Planes; (accessed 01/02/)
    • Biello, D. Scientific American. Navy Green: Military Investigates Biofuels to Power Its Ships and Planes; http://www.scientificamerican.com/ article.cfm?id=navy-investigates-biofuels-to-power-ships-airplanes (accessed 01/02/ 2012).
    • (2012)
    • Biello, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.