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Volumn , Issue 13, 2008, Pages 2273-2287

Further uses of pyrrole-based dienoxysilane synthons: A full aldol approach to azabicyclo[x.2.1]alkane systems

Author keywords

Aldol reactions; Asymmetric synthesis; Diastereoselectivity; Ketones; N heterocycles

Indexed keywords


EID: 48249131089     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800040     Document Type: Article
Times cited : (20)

References (62)
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    • for A-315675, see: D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453;
    • b) for A-315675, see: D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453;
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    • 0034740839 scopus 로고    scopus 로고
    • 2-Azabicyclo[2.2.1]heptane (2-azanorbornane) and 6-azabicyclo[ 3.2.1]octane (normorphan) systems represent key structural units found in a number of biologically important natural and synthetic products. See, for example, 2-azabicyclo[2.2.1]heptanes: a) C. D. Cox, J. R. Malpass, J. Gordon, A. Rosen, J. Chem. Soc. Perkin Trans. 1 2001, 2372-2379;
    • 2-Azabicyclo[2.2.1]heptane (2-azanorbornane) and 6-azabicyclo[ 3.2.1]octane (normorphan) systems represent key structural units found in a number of biologically important natural and synthetic products. See, for example, 2-azabicyclo[2.2.1]heptanes: a) C. D. Cox, J. R. Malpass, J. Gordon, A. Rosen, J. Chem. Soc. Perkin Trans. 1 2001, 2372-2379;
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    • 0026318360 scopus 로고    scopus 로고
    • for 6-azabicyclo[3.2.1]octanes, see: f D. J. Triggle, Y. W. Kwon, P. Abraham, J. B. Pitner, S. W. Mascarella, F. I. Carroll, J. Med. Chem. 1991, 34, 3164-3171;
    • for 6-azabicyclo[3.2.1]octanes, see: f) D. J. Triggle, Y. W. Kwon, P. Abraham, J. B. Pitner, S. W. Mascarella, F. I. Carroll, J. Med. Chem. 1991, 34, 3164-3171;
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    • 8744245317 scopus 로고    scopus 로고
    • for extended (vinylogous) donors, see: g
    • for extended (vinylogous) donors, see: g) J. Cong-Dung, B. L. Pagenkopf, Org. Lett. 2004, 6, 4097-4099;
    • (2004) Org. Lett , vol.6 , pp. 4097-4099
    • Cong-Dung, J.1    Pagenkopf, B.L.2
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    • 53749104441 scopus 로고    scopus 로고
    • Symmetrical, achiral ketones like, for example, acetone and di-ethyl ketone were also pertinent substrates, leading to the expected silylated tertiary carbinol adducts in high isolated yields
    • Symmetrical, achiral ketones like, for example, acetone and di-ethyl ketone were also pertinent substrates, leading to the expected silylated tertiary carbinol adducts in high isolated yields.
  • 46
    • 53749107246 scopus 로고    scopus 로고
    • Under these conditions, silicon transfer from the donor to the acceptor partner is seemingly hampered by the carboxyalkyl group α to the ketone carbonyl group
    • Under these conditions, silicon transfer from the donor to the acceptor partner is seemingly hampered by the carboxyalkyl group α to the ketone carbonyl group.
  • 53
    • 0033538635 scopus 로고    scopus 로고
    • Modified, direct Swern oxidation of primary silyl ethers is a known, useful option, see
    • Modified, direct Swern oxidation of primary silyl ethers is a known, useful option, see: A. Rodríguez, M. Nomen, B. W. Spur, J. J. Godfroid, Tetrahedron Lett. 1999, 40, 5161-5164.
    • (1999) Tetrahedron Lett , vol.40 , pp. 5161-5164
    • Rodríguez, A.1    Nomen, M.2    Spur, B.W.3    Godfroid, J.J.4
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    • 53749087098 scopus 로고    scopus 로고
    • Under these conditions, a significant amount of its γ-lactone form was also obtained
    • Under these conditions, a significant amount of its γ-lactone form was also obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.