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Volumn 68, Issue 9, 2003, Pages 3511-3521

A systematic study of the hydride reduction of cyclopropyl ketones with structurally simplified substrates. Highly stereoselective reductions of trans-substituted cyclopropyl ketones via the bisected s-cis conformation

Author keywords

[No Author keywords available]

Indexed keywords

PROBABILITY DENSITY FUNCTION; REDUCTION; STEREOCHEMISTRY;

EID: 0037414487     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030019v     Document Type: Article
Times cited : (33)

References (54)
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    • Zhang, X.1    Hodgetts, K.2    Rachwal, S.3    Zhao, H.4    Wasley, J.W.F.5    Craven, K.6    Brodbeck, R.7    Kieltyka, A.8    Hoffman, D.9    Bacolod, M.D.10    Girard, B.11    Tran, J.12    Thurkauf, A.13
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    • Examples of synthesis of chiral cyclopropanes from chiral synthons: (a) Yamanoi, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 1181-1184. (b) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804. (c) Pirrung, M. C.; Dunlap, S. E.; Trinks, V. P. Helv. Chim. Acta 1989, 72, 1301-1310. (d) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103. (e) Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657. (f) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656.
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    • Examples of synthesis of chiral cyclopropanes from chiral synthons: (a) Yamanoi, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 1181-1184. (b) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804. (c) Pirrung, M. C.; Dunlap, S. E.; Trinks, V. P. Helv. Chim. Acta 1989, 72, 1301-1310. (d) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103. (e) Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657. (f) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656.
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    • Examples of synthesis of chiral cyclopropanes from chiral synthons: (a) Yamanoi, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 1181-1184. (b) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804. (c) Pirrung, M. C.; Dunlap, S. E.; Trinks, V. P. Helv. Chim. Acta 1989, 72, 1301-1310. (d) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103. (e) Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657. (f) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656.
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    • Examples of synthesis of chiral cyclopropanes from chiral synthons: (a) Yamanoi, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 1181-1184. (b) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804. (c) Pirrung, M. C.; Dunlap, S. E.; Trinks, V. P. Helv. Chim. Acta 1989, 72, 1301-1310. (d) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103. (e) Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657. (f) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656.
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  • 15
    • 0000163873 scopus 로고    scopus 로고
    • Examples of synthesis of chiral cyclopropanes from chiral synthons: (a) Yamanoi, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 1181-1184. (b) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804. (c) Pirrung, M. C.; Dunlap, S. E.; Trinks, V. P. Helv. Chim. Acta 1989, 72, 1301-1310. (d) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103. (e) Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657. (f) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656.
    • (1997) J. Org. Chem. , vol.62 , pp. 6638-6657
    • Critcher, D.J.1    Connolly, S.2    Wills, M.3
  • 16
    • 0034612132 scopus 로고    scopus 로고
    • Examples of synthesis of chiral cyclopropanes from chiral synthons: (a) Yamanoi, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 1181-1184. (b) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804. (c) Pirrung, M. C.; Dunlap, S. E.; Trinks, V. P. Helv. Chim. Acta 1989, 72, 1301-1310. (d) Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103. (e) Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657. (f) Takemoto, Y.; Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka, T. Tetrahedron Lett. 2000, 41, 3653-3656.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3653-3656
    • Takemoto, Y.1    Baba, Y.2    Saha, G.3    Nakao, S.4    Iwata, C.5    Tanaka, T.6    Ibuka, T.7
  • 44
    • 0242681793 scopus 로고    scopus 로고
    • note
    • Examples of stereochemical reversal in the reduction of cyclopropyl ketones when an electrophilic reducing agent DIBAL-H was used: see ref 8d,e,f.
  • 46
    • 0000163873 scopus 로고    scopus 로고
    • Stereocontrol in carbon - nucleophile additions to trans-cyclopropyl carbonyls is also known to be exceedingly difficult, see: Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657.
    • (1997) J. Org. Chem. , vol.62 , pp. 6638-6657
    • Critcher, D.J.1    Connolly, S.2    Wills, M.3
  • 47
    • 2142858450 scopus 로고
    • The stereochemistries of the reduction products were determined by the modified Mosher's method (Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc, 1991, 113, 4092-4096); see the Supporting Information.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092-4096
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 48
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    • note
    • 3 did not suggest a stable conformation in solution, and crystals of the transsubstituted ketones 1a-e and 2 suitable for X-ray crystallographic analysis were not obtained.
  • 50
    • 0001181977 scopus 로고
    • The conformation of the transition state and the intermediate can be strongly influenced by conformational effects which stabilize the ground state conformation, for examples see: (a) Pothier, N.; Goldstein, S.; Deslongchamps, P. Helv. Chim Acta 1992, 75, 604-620.
    • (1992) Helv. Chim Acta , vol.75 , pp. 604-620
    • Pothier, N.1    Goldstein, S.2    Deslongchamps, P.3


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