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Volumn , Issue 6, 2004, Pages 983-986

Diastereoselective synthesis of trans-ethynyl N-tert- butanesulfinylaziridines

Author keywords

Asymmetric synthesis; Aziridines; Carbenoid; Chiral resolution; Zinc

Indexed keywords

AZIRIDINE DERIVATIVE; IMINE;

EID: 3142777628     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820058     Document Type: Article
Times cited : (49)

References (46)
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    • For recent synthetic applications of alkynylaziridines see: (a) Ohno, H.; Hamaguchi, H.; Tanaka, T. J. Org. Chem. 2001, 66, 1867. (b) Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2000, 2, 2161. (c) Ohno, H.; Toda, A.; Fujii, N.; Takemoto, Y.; Tanaka, T.; Ibuka, T. Tetrahedron 2000, 56, 2811. (d) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 349.
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    • For recent synthetic applications of alkynylaziridines see: (a) Ohno, H.; Hamaguchi, H.; Tanaka, T. J. Org. Chem. 2001, 66, 1867. (b) Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2000, 2, 2161. (c) Ohno, H.; Toda, A.; Fujii, N.; Takemoto, Y.; Tanaka, T.; Ibuka, T. Tetrahedron 2000, 56, 2811. (d) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 349.
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    • For recent synthetic applications of alkynylaziridines see: (a) Ohno, H.; Hamaguchi, H.; Tanaka, T. J. Org. Chem. 2001, 66, 1867. (b) Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2000, 2, 2161. (c) Ohno, H.; Toda, A.; Fujii, N.; Takemoto, Y.; Tanaka, T.; Ibuka, T. Tetrahedron 2000, 56, 2811. (d) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 349.
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    • Ohno, H.1    Toda, A.2    Fujii, N.3    Takemoto, Y.4    Tanaka, T.5    Ibuka, T.6
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    • 0033534507 scopus 로고    scopus 로고
    • For recent synthetic applications of alkynylaziridines see: (a) Ohno, H.; Hamaguchi, H.; Tanaka, T. J. Org. Chem. 2001, 66, 1867. (b) Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2000, 2, 2161. (c) Ohno, H.; Toda, A.; Fujii, N.; Takemoto, Y.; Tanaka, T.; Ibuka, T. Tetrahedron 2000, 56, 2811. (d) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 349.
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    • note
    • 4 and concentrated in vacuo. The residual brownish oil was purified by flash chromatography over silica gel to give the corresponding diastereomerically pure trans-ethynyl N-sulfinylaziridine (±)-3.
  • 29
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    • For the carbenoid character of analogous organolithium derivatives see: (a) Jones, G. B.; Wright, J. M.; Plourde, G. W. II; Hynd, G.; Huber, R. S.; Mathews, J. E. J. Am. Chem. Soc. 2000, 122, 1937. (b) Wright, J. M.; Jones, G. B. Tetrahedron Lett. 1999, 40, 7605. (c) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481. (d) McPhee, M. M.; Kerwin, S. M. J. Org. Chem. 1996, 61, 9385. (e) Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791. (f) Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655.
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    • For the carbenoid character of analogous organolithium derivatives see: (a) Jones, G. B.; Wright, J. M.; Plourde, G. W. II; Hynd, G.; Huber, R. S.; Mathews, J. E. J. Am. Chem. Soc. 2000, 122, 1937. (b) Wright, J. M.; Jones, G. B. Tetrahedron Lett. 1999, 40, 7605. (c) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481. (d) McPhee, M. M.; Kerwin, S. M. J. Org. Chem. 1996, 61, 9385. (e) Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791. (f) Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655.
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    • For the carbenoid character of analogous organolithium derivatives see: (a) Jones, G. B.; Wright, J. M.; Plourde, G. W. II; Hynd, G.; Huber, R. S.; Mathews, J. E. J. Am. Chem. Soc. 2000, 122, 1937. (b) Wright, J. M.; Jones, G. B. Tetrahedron Lett. 1999, 40, 7605. (c) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481. (d) McPhee, M. M.; Kerwin, S. M. J. Org. Chem. 1996, 61, 9385. (e) Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791. (f) Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655.
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    • For the carbenoid character of analogous organolithium derivatives see: (a) Jones, G. B.; Wright, J. M.; Plourde, G. W. II; Hynd, G.; Huber, R. S.; Mathews, J. E. J. Am. Chem. Soc. 2000, 122, 1937. (b) Wright, J. M.; Jones, G. B. Tetrahedron Lett. 1999, 40, 7605. (c) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481. (d) McPhee, M. M.; Kerwin, S. M. J. Org. Chem. 1996, 61, 9385. (e) Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791. (f) Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655.
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    • For the carbenoid character of analogous organolithium derivatives see: (a) Jones, G. B.; Wright, J. M.; Plourde, G. W. II; Hynd, G.; Huber, R. S.; Mathews, J. E. J. Am. Chem. Soc. 2000, 122, 1937. (b) Wright, J. M.; Jones, G. B. Tetrahedron Lett. 1999, 40, 7605. (c) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481. (d) McPhee, M. M.; Kerwin, S. M. J. Org. Chem. 1996, 61, 9385. (e) Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791. (f) Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655.
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    • Jones, G.B.1    Huber, R.S.2    Mathews, J.E.3
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    • For the carbenoid character of analogous organolithium derivatives see: (a) Jones, G. B.; Wright, J. M.; Plourde, G. W. II; Hynd, G.; Huber, R. S.; Mathews, J. E. J. Am. Chem. Soc. 2000, 122, 1937. (b) Wright, J. M.; Jones, G. B. Tetrahedron Lett. 1999, 40, 7605. (c) Hynd, G.; Jones, G. B.; Plourde, G. W. II; Wright, J. M. Tetrahedron Lett. 1999, 40, 4481. (d) McPhee, M. M.; Kerwin, S. M. J. Org. Chem. 1996, 61, 9385. (e) Jones, G. B.; Huber, R. S.; Mathews, J. E. J. Chem. Soc., Chem. Commun. 1995, 1791. (f) Huber, R. S.; Jones, G. B. Tetrahedron Lett. 1994, 35, 2655.
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    • note
    • CCDC 230643 contains the supplementary crystallographic data for compound (±)-3g. These data can be obtained free of charge via www.ccdc.ac.uk/conts/retrieving.html [or from Cambridge Cystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax:+44(1223)336033; or deposit@ccdc.cam.ac.uk].
  • 36
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    • note
    • In the case of N-sulfonylimines, for which low selectivities are obtained (see ref. 10a), such a coordination of the zinc by the sulfonyl group has not been envisaged because of weak Lewis basicity of both nitrogen and oxygen atoms.
  • 44
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    • For a recent review on multiple stereoselectivity see: Kolodiazhnyi, O. I. Tetrahedron 2003, 59, 5953.
    • (2003) Tetrahedron , vol.59 , pp. 5953
    • Kolodiazhnyi, O.I.1


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