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Volumn 15, Issue 7, 2013, Pages 1658-1661

Intermolecular alkyl radical additions to enantiopure N-tert-butanesulfinyl aldimines

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; AMINE; IMINE; SULFONIUM DERIVATIVE;

EID: 84875918642     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400439g     Document Type: Article
Times cited : (34)

References (63)
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    • Nugent, T.C.1    El-Shazly, M.2
  • 18
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    • references cited therein
    • Bazin, S.; Feray, L.; Bertrand, M. Chimia 2006, 60, 260 and references cited therein
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    • Bazin, S.1    Feray, L.2    Bertrand, M.3
  • 24
    • 84858112333 scopus 로고    scopus 로고
    • references cited therein
    • Friestad, G. K. Top. Curr. Chem. 2012, 320, 61 and references cited therein
    • (2012) Top. Curr. Chem. , vol.320 , pp. 61
    • Friestad, G.K.1
  • 25
    • 84862575222 scopus 로고    scopus 로고
    • Miyabe, H. Synlett 2012, 23, 1709
    • (2012) Synlett , vol.23 , pp. 1709
    • Miyabe, H.1
  • 52
    • 84875961546 scopus 로고    scopus 로고
    • Also see ref 15a
    • Also see ref 15a.
  • 54
    • 65549171630 scopus 로고    scopus 로고
    • The reduction process was not observed using zincates (Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron Lett. 2009, 50, 3198), which provided a similar yield (90%) but lower stereoselectivity (94:6 dr) than those indicated in entry 3 in Table 1 (91%; >98:2 dr)
    • (2009) Tetrahedron Lett. , vol.50 , pp. 3198
    • Almansa, R.1    Guijarro, D.2    Yus, M.3
  • 58
    • 84875936525 scopus 로고    scopus 로고
    • PCT Int Appl. WO 2012/009226 A1
    • It is remarkable that the acid resulting in the hydrolysis of 5Da has been used for obtaining antidiabetic agents (See:Demong, D.;Miller, M. W.; Dai,X.; Stamford,A. PCT Int Appl. (2012)WO 2012/009226 A1) and substituted hydroxamic acids employed as inhibitors ofHDCAC6(histone deacetylase 6).
    • (2012)
    • Demong, D.1    Miller, M.W.2    Dai, X.3    Stamford, A.4
  • 59
    • 84875965411 scopus 로고    scopus 로고
    • PCT Int Appl. WO2011/106632 A1
    • (See: Blackburn, C.; Gigstad, K. M.; Harrison, S. J.; Xu, H. PCT Int Appl. (2011) WO2011/106632 A1). In these patents, the addition of i -PrLi to an N-tert -butanesulfinylaldimine is the key step in the synthesis of the starting acid. It requires starting from a t -Bu ester (to avoid nucleophilic attack to the carbonyl group) and yields a mixture of diastereoisomers that, once separated, give a 46% yield of the appropriated one. By contrast, in our case, we perform the radical addition starting from the methyl ester (3D) with complete control of the stereoselectivity and quantitative yield (entry 4, Table 3).
    • (2011)
    • Blackburn, C.1    Gigstad, K.M.2    Harrison, S.J.3    Xu, H.4
  • 63
    • 57049088500 scopus 로고    scopus 로고
    • The absolute configuration of the new chiral center at the major diastereoisomer 5Aa has been established as R by the coincidence in the specific rotation of amine hydrochloride 6Aa, with that previously reported: Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron: Asymmetry 2008, 19 (603) 2484
    • (2008) Tetrahedron: Asymmetry , vol.19 , Issue.603 , pp. 2484
    • Almansa, R.1    Guijarro, D.2    Yus, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.