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Volumn 124, Issue 51, 2002, Pages 15255-15266

A highly cis-selective synthesis of 2-ethynylaziridines by intramolecular amination of chiral bromoallenes: Improvement of stereoselectivity based on the computational investigation

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; PROBABILITY DENSITY FUNCTION; SODIUM COMPOUNDS; SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 0347928822     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0262277     Document Type: Article
Times cited : (52)

References (64)
  • 28
    • 33847090113 scopus 로고
    • 2-Ethynylaziridines are also known as a versatile building block for the synthesis of IH-azepine: Mannisse, N.; Chuche, J. J. Am. Chem. Soc. 1977, 99, 1272-1273.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 1272-1273
    • Mannisse, N.1    Chuche, J.2
  • 35
    • 1542396379 scopus 로고    scopus 로고
    • (b) Ohno, H.; Toda. A.; Takemoto, Y.; Fujii, N.; lbuka, T. J. Chem. Soc., Perkin Trans. 1 1999, 2949-2962. For another related. synthesis, see: Chen, S.-T.; Fang; J.-M. J. Org. Chem. 1997, 62, 4347-4357.
    • (1997) J. Org. Chem. , vol.62 , pp. 4347-4357
    • Chen, S.-T.1    Fang, J.-M.2
  • 36
    • 0025072488 scopus 로고
    • In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
    • (1990) J. Org. Chem. , vol.55 , pp. 3772-3787
    • Garner, P.1    Park, J.M.2
  • 37
    • 0000051661 scopus 로고    scopus 로고
    • In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
    • (1996) J. Org. Chem. , vol.61 , pp. 9631-9636
    • D'Aniello, F.1    Schoenfelder, A.2    Mann, A.3    Taddei, M.4
  • 38
    • 0041407526 scopus 로고    scopus 로고
    • In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1806-1807
    • Frantz, D.E.1    Carreira, E.M.2
  • 39
    • 0041780219 scopus 로고    scopus 로고
    • In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
    • (2000) Org. Lett. , vol.2 , pp. 4233-4236
    • Boyall, D.1    Ĺpez, F.2    Sasaki, H.3    Frantz, D.4    Carreira, E.M.5
  • 40
    • 0035954878 scopus 로고    scopus 로고
    • A portion of this study was reported in a preliminary communication: Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2001, 3, 2269-2271.
    • (2001) Org. Lett. , vol.3 , pp. 2269-2271
    • Ohno, H.1    Hamaguchi, H.2    Tanaka, T.3
  • 41
    • 0345826419 scopus 로고    scopus 로고
    • note
    • 13b For details, see the Supporting Information.
  • 43
    • 0345826418 scopus 로고    scopus 로고
    • note
    • For synthesis of bromoallenes 7g and 9g bearing a methyl group, see the Supporting Information.
  • 44
    • 0000596010 scopus 로고    scopus 로고
    • For a methanesulfonic acid mediated ring-opening reaction of vinylaziridines, see: (a) Tamamura, H.; Yamashita, M.; Muramatsu, H.; Ohno, H.; Ibuka, T.; Otaka, A.; Fujii, N. Chem. Commun. 1997, 23, 2327-2328. (b) Tamamura, H.; Yamashita, M.; Nakajima, Y.; Sakano, K.; Otaka, A.; Ohno, H.; Ibuka, T.; Fujii, N. J. Chem. Soc., Perkin Trans. 1 1999, 2983-2996.
    • (1997) Chem. Commun. , vol.23 , pp. 2327-2328
    • Tamamura, H.1    Yamashita, M.2    Muramatsu, H.3    Ohno, H.4    Ibuka, T.5    Otaka, A.6    Fujii, N.7
  • 46
    • 0001278389 scopus 로고
    • (a) Hennion, G. F.; Maloney, D. E. J. Am. Chem. Soc. 1951, 73, 4735-4737. (b) Shiner, V. J.; Humphrey, J. S., Jr. J. Am. Chem. Soc. 1967, 89, 622-630. See also ref 6a and b.
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 4735-4737
    • Hennion, G.F.1    Maloney, D.E.2
  • 47
    • 0347087802 scopus 로고
    • See also ref 6a and b
    • (a) Hennion, G. F.; Maloney, D. E. J. Am. Chem. Soc. 1951, 73, 4735-4737. (b) Shiner, V. J.; Humphrey, J. S., Jr. J. Am. Chem. Soc. 1967, 89, 622-630. See also ref 6a and b.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 622-630
    • Shiner, V.J.1    Humphrey J.S., Jr.2
  • 49
    • 0347718190 scopus 로고    scopus 로고
    • note
    • Although the 2,3-cis selective synthesis of 2-ethynylaziridines was possible by the treatment of bromoallenes with NaH/DMF for a prolonged reaction time, yields of the one-pot aziridination-equilibration reaction are unsatisfactory.
  • 50
    • 0001219079 scopus 로고    scopus 로고
    • The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
    • (1997) J. Org. Chem. , vol.62 , pp. 999-1015
    • Ibuka, T.1    Mimura, N.2    Aoyama, H.3    Akaji, M.4    Ohno, H.5    Miwa, Y.6    Taga, T.7    Nakai, K.8    Tamamura, H.9    Fujii, N.10    Yamamoto, Y.11
  • 51
    • 0000831199 scopus 로고    scopus 로고
    • The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
    • (1997) J. Org. Chem. , vol.62 , pp. 2982-2991
    • Ibuka, T.1    Mimura, N.2    Ohno, H.3    Nakai, K.4    Akaji, M.5    Habashita, H.6    Tamamura, H.7    Miwa, Y.8    Taga, T.9    Fujii, N.10    Yamamoto, Y.11
  • 52
    • 33748720246 scopus 로고    scopus 로고
    • The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3703-3716
    • Ohno, H.1    Ishii, K.2    Honda, A.3    Tamamura, H.4    Fujii, N.5    Takemoto, Y.6    Ibuka, T.7
  • 53
    • 0033547966 scopus 로고    scopus 로고
    • The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1331-1334
    • Ohno, H.1    Toda, A.2    Fujii, N.3    Miwa, Y.4    Taga, T.5    Yamaoka, Y.6    Osawa, E.7    Ibuka, T.8
  • 63
    • 0346457465 scopus 로고    scopus 로고
    • note
    • The calculations at B3LYP/6-31G level gave similar energy differences [e.g., ΔG (trans-B-cis-B) = 3.92 kcal/mol, vs 4.35 kcal/mol] and similar transition structures with the ones at B3LYP/6-31+G(d). Compare cis-B1 in Figure 3 with cis-B in Figure 4.
  • 64
    • 0347087796 scopus 로고    scopus 로고
    • note
    • For synthesis of the starting amino alcohols, see the Supporting Information of ref 7d.


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