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Volumn 20, Issue 13, 2009, Pages 1561-1567

Copper-catalyzed asymmetric conjugate addition of Grignard reagents to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes

Author keywords

[No Author keywords available]

Indexed keywords

1 (N,N DIISOPROPYLCARBAMOYLOXY) 1 TOSYL ALKENE; ALKANE; ALKENE DERIVATIVE; BROMIDE; COPPER; GRIGNARD REAGENT; LIGAND; MAGNESIUM; UNCLASSIFIED DRUG;

EID: 67651108962     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.06.001     Document Type: Article
Times cited : (8)

References (24)
  • 6
    • 0027972828 scopus 로고
    • Copper-catalyzed ACA on substrate containing chiral auxiliary group was known:
    • Copper-catalyzed ACA on substrate containing chiral auxiliary group was known:. Lander P.A., and Hegedus L.S. J. Am. Chem. Soc. 116 (1994) 8126-8132
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8126-8132
    • Lander, P.A.1    Hegedus, L.S.2
  • 7
    • 67651107703 scopus 로고    scopus 로고
    • note
    • It is rather important to carry out these experiments in diethyl ether to achieve good yield and regioselectivity.
  • 11
    • 67651103411 scopus 로고    scopus 로고
    • note
    • The low diastereoselectivity of the conversion from 10 to 6 with TMEDA/s-BuLi indicated a close resemblance between the phenyl group and the isopropenyl group for the diamine-assisted enantioselective lithiation chemistry on α-stereogenic carbamate substrates.
  • 12
    • 67651094669 scopus 로고    scopus 로고
    • note
    • The er on C2 from the deprotonation with TMEDA/s-BuLi was not the same for products 6 and 7. This is because (S)-phenyloxiranes of different enantiomeric purities from different batches were applied as the starting material.
  • 22
    • 37349038497 scopus 로고    scopus 로고
    • The relationship between the double bond geometry of typical Michael receptors and the enantioselectivity of the copper-catalyzed ACA has been investigated; see for example:
    • The relationship between the double bond geometry of typical Michael receptors and the enantioselectivity of the copper-catalyzed ACA has been investigated; see for example:. Vuagnoux-d'Augustin M., and Alexakis A. Eur. J. Org. Chem. (2007) 5852-5860
    • (2007) Eur. J. Org. Chem. , pp. 5852-5860
    • Vuagnoux-d'Augustin, M.1    Alexakis, A.2
  • 23
    • 54749112196 scopus 로고    scopus 로고
    • It is known that certain phosphites tolerate Grignard reagents:
    • It is known that certain phosphites tolerate Grignard reagents:. Robert T., Velder J., and Schmalz H.-G. Angew. Chem., Int. Ed. 47 (2008) 7718-7721
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7718-7721
    • Robert, T.1    Velder, J.2    Schmalz, H.-G.3
  • 24
    • 67651084172 scopus 로고    scopus 로고
    • note
    • Chiral HPLC data of substrate 5b on a Eurocel 01 (5 μm, 250 × 4.6 mm, Knauer): i-PrOH/n-hexane: 1:150, 0.6 mL/min, 55 min; Under the same condition, substrate 5a shows a very broad peak with a retention time of more than 120 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.