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Volumn 118, Issue 29, 1996, Pages 6897-6907

Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DIAZONIUM COMPOUND; RHODIUM DERIVATIVE;

EID: 0029945485     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9604931     Document Type: Article
Times cited : (438)

References (116)
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    • For examples of naturally occurring cyclopropanamino acids, see: (a) Sakamura, S.; Ichehara, A.; Shiraishi, K.; Sato, K.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Mitchell, R. E. Phytochemistty 1985, 24, 1485. (c) Hoffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (d) Wakamiya, T.; Nakamoto, H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (e) Wakamiya, T.; Oda, Y.; Fujita, H.; Shiba, T. Tetrahedron Lett. 1986, 27, 2143.
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    • For examples of naturally occurring cyclopropanamino acids, see: (a) Sakamura, S.; Ichehara, A.; Shiraishi, K.; Sato, K.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Mitchell, R. E. Phytochemistty 1985, 24, 1485. (c) Hoffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (d) Wakamiya, T.; Nakamoto, H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (e) Wakamiya, T.; Oda, Y.; Fujita, H.; Shiba, T. Tetrahedron Lett. 1986, 27, 2143.
    • (1985) Phytochemistty , vol.24 , pp. 1485
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    • For examples of naturally occurring cyclopropanamino acids, see: (a) Sakamura, S.; Ichehara, A.; Shiraishi, K.; Sato, K.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Mitchell, R. E. Phytochemistty 1985, 24, 1485. (c) Hoffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (d) Wakamiya, T.; Nakamoto, H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (e) Wakamiya, T.; Oda, Y.; Fujita, H.; Shiba, T. Tetrahedron Lett. 1986, 27, 2143.
    • (1982) S. Plant Physiol. , vol.70 , pp. 195
    • Hoffman, N.E.1    Yang, S.F.2    Ichihara, A.3    Sakamura4
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    • For examples of naturally occurring cyclopropanamino acids, see: (a) Sakamura, S.; Ichehara, A.; Shiraishi, K.; Sato, K.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Mitchell, R. E. Phytochemistty 1985, 24, 1485. (c) Hoffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (d) Wakamiya, T.; Nakamoto, H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (e) Wakamiya, T.; Oda, Y.; Fujita, H.; Shiba, T. Tetrahedron Lett. 1986, 27, 2143.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4411
    • Wakamiya, T.1    Nakamoto, H.2    Shiba, T.3
  • 7
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    • For examples of naturally occurring cyclopropanamino acids, see: (a) Sakamura, S.; Ichehara, A.; Shiraishi, K.; Sato, K.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Mitchell, R. E. Phytochemistty 1985, 24, 1485. (c) Hoffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (d) Wakamiya, T.; Nakamoto, H.; Shiba, T. Tetrahedron Lett. 1984, 25, 4411. (e) Wakamiya, T.; Oda, Y.; Fujita, H.; Shiba, T. Tetrahedron Lett. 1986, 27, 2143.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2143
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    • For a preliminary account of portions of this work, see: (a) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243. (b) Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett., in press.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7243
    • Davies, H.M.L.1    Hutcheson, D.K.2
  • 70
    • 0027488634 scopus 로고    scopus 로고
    • in press
    • For a preliminary account of portions of this work, see: (a) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243. (b) Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett., in press.
    • Tetrahedron Lett.
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    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • (b) Davies, H. M. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, pp 1031-1068.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1031-1068
    • Davies, H.M.L.1
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    • note
    • 1H NMR using tris[3-[(heptafluoropropyl)hydroxymethylene]-(-)-camphorato]praseodymium-(III) as a chiral shift reagent and intergration of the split methoxy signal, or by HPLC using a Diacel Chiralcel OJ analytical column (see ref 29).
  • 86
    • 8944241513 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 12a was determined by comparison of the optical rotation of 12a with that of an authentic sample (see ref 16).
  • 87
    • 8944259621 scopus 로고    scopus 로고
    • note
    • The major enantiomer for 12b-d was assigned as (1S,2S) on the basis of the ORD spectra of 12b-d similar to that of 12a.
  • 89
    • 8944252053 scopus 로고    scopus 로고
    • note
    • The absolute configurations for 13 and 14 have been assigned on the basis of the ORD spectra of these compounds similar to that of 12a.
  • 90
    • 8944223722 scopus 로고    scopus 로고
    • note
    • The absolute configurations assigned for 15-20 and 23 are tentative and are based on the proposed transition state model for the asymmetric induction.
  • 108
    • 0002578608 scopus 로고
    • Ojima, I., Ed.; VCH Publishers: New York
    • Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 159-202.
    • (1993) Catalytic Asymmetric Synthesis , pp. 159-202
    • Jacobsen, E.N.1
  • 109
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    • note
    • Calculations were carried out on a CAChe STEREO Worksystem using the standard software programs supplied by CAChe Scientific, Beaverton, OR.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.