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Volumn 75, Issue 18, 2010, Pages 6308-6311

Stereoselective α-aminoallylation of aldehydes with chiral tert -butanesulfinamides and allyl bromides

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL BROMIDE; CONCISE SYNTHESIS; HIGH YIELD; INDIUM METAL; NATURALLY OCCURRING; STEREO-SELECTIVE; SYNTHETIC UTILITY;

EID: 77956505380     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101379u     Document Type: Article
Times cited : (88)

References (47)
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    • For reviews on the asymmetric synthesis of amines via N-tert -butanesulfinylimines, see
    • For reviews on the asymmetric synthesis of amines via N-tert -butanesulfinylimines, see: Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984
    • (2002) Acc. Chem. Res. , vol.35 , pp. 984
    • Ellman, J.A.1    Owens, T.D.2    Tang, T.P.3
  • 33
    • 77956513376 scopus 로고    scopus 로고
    • note
    • It is worth noting that in the α-aminoallylation with ammonia, a large excess of ammonia was crucial to obtain high chemoselectivity. See: Reference 5c.
  • 35
    • 70249117898 scopus 로고    scopus 로고
    • Very recently, it has been shown that TFA promotes efficiently the intramolecular indium-mediated allylation of chiral hydrazones. See
    • Very recently, it has been shown that TFA promotes efficiently the intramolecular indium-mediated allylation of chiral hydrazones. See: Samanta, D.; Kargbo, R. B.; Cook, G. R. J. Org. Chem. 2009, 74, 7183
    • (2009) J. Org. Chem. , vol.74 , pp. 7183
    • Samanta, D.1    Kargbo, R.B.2    Cook, G.R.3
  • 36
    • 2942628421 scopus 로고    scopus 로고
    • 3 increases both the stereoselectivity and the rate of the indium-mediated allylation of chiral hydrazones. See
    • 3 increases both the stereoselectivity and the rate of the indium-mediated allylation of chiral hydrazones. See: Cook, G. R.; Maity, B. C.; Kargbo, R. Org. Lett. 2004, 6, 1741
    • (2004) Org. Lett. , vol.6 , pp. 1741
    • Cook, G.R.1    Maity, B.C.2    Kargbo, R.3
  • 37
    • 0033582571 scopus 로고    scopus 로고
    • 4 it is an excellent water scavenger and catalyst for the formation of N-tert -butanesulfinylimines, see
    • 4 it is an excellent water scavenger and catalyst for the formation of N-tert -butanesulfinylimines, see: Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278
    • (1999) J. Org. Chem. , vol.64 , pp. 1278
    • Liu, G.1    Cogan, D.A.2    Owens, T.D.3    Tang, T.P.4    Ellman, J.A.5
  • 38
    • 33846204404 scopus 로고    scopus 로고
    • 4 has also been successfully used in a one-pot protocol for the formation and reduction of N-tert -butanesulfinylketoimines, see
    • 4 has also been successfully used in a one-pot protocol for the formation and reduction of N-tert -butanesulfinylketoimines, see: Tanuwidjaja, J.; Peltier, H. M.; Ellman, J. A. J. Org. Chem. 2007, 72, 626
    • (2007) J. Org. Chem. , vol.72 , pp. 626
    • Tanuwidjaja, J.1    Peltier, H.M.2    Ellman, J.A.3
  • 39
    • 49149123060 scopus 로고    scopus 로고
    • It is known that the stereochemical outcome of the Zn/In-mediated allylation of N-tert -butanesulfinyl imines can be highly dependent on the presence of Lewis acids or bases. See
    • It is known that the stereochemical outcome of the Zn/In-mediated allylation of N-tert -butanesulfinyl imines can be highly dependent on the presence of Lewis acids or bases. See: Lin, G.-Q.; Xu, M.-H.; Zhong, Y. W.; Sun, X.-W. Acc. Chem. Res. 2008, 41, 831
    • (2008) Acc. Chem. Res. , vol.41 , pp. 831
    • Lin, G.-Q.1    Xu, M.-H.2    Zhong, Y.W.3    Sun, X.-W.4
  • 42
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    • NMR analysis by comparison to diastereomer mixture standards prepared according to
    • NMR analysis by comparison to diastereomer mixture standards prepared according to: Brak, K.; Barret, K. T.; Ellman, J. A. J. Org. Chem. 2009, 74, 3606
    • (2009) J. Org. Chem. , vol.74 , pp. 3606
    • Brak, K.1    Barret, K.T.2    Ellman, J.A.3
  • 43
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    • note
    • Crystal data (excluding structure factors) deposited at the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 779151.
  • 45
    • 77956523928 scopus 로고    scopus 로고
    • note
    • 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.