메뉴 건너뛰기




Volumn 14, Issue 23, 2003, Pages 3657-3666

Novozym-435-catalyzed efficient preparation of (1S)-ethenyl and ethynyl 2,3-allenols and (1R)-ethenyl and ethynyl 2,3-allenyl acetates with high enantiomeric excess

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLENE DERIVATIVE; CARBON; FUNGAL ENZYME; ISOENZYME; LIPASE B; NOVOZYM 435; UNCLASSIFIED DRUG;

EID: 0345447577     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.09.048     Document Type: Article
Times cited : (26)

References (45)
  • 3
    • 25544454453 scopus 로고    scopus 로고
    • For the reaction of functionalized allenes, see: (a) Zimmer, R.; Dinesh, U.; Nandanan, E.; Khan, F. A.; Chem. Rev. 2000, 100, 3065; (b) Ma, S.; Li, L. Synlett 2001, 8, 1206; (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (d) Ma, S.; Zhao, S. Org. Lett. 2000, 16, 2495.
    • (2000) Chem. Rev. , vol.100 , pp. 3065
    • Zimmer, R.1    Dinesh, U.2    Nandanan, E.3    Khan, F.A.4
  • 4
    • 0034908562 scopus 로고    scopus 로고
    • For the reaction of functionalized allenes, see: (a) Zimmer, R.; Dinesh, U.; Nandanan, E.; Khan, F. A.; Chem. Rev. 2000, 100, 3065; (b) Ma, S.; Li, L. Synlett 2001, 8, 1206; (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (d) Ma, S.; Zhao, S. Org. Lett. 2000, 16, 2495.
    • (2001) Synlett , vol.8 , pp. 1206
    • Ma, S.1    Li, L.2
  • 5
    • 0032483548 scopus 로고    scopus 로고
    • For the reaction of functionalized allenes, see: (a) Zimmer, R.; Dinesh, U.; Nandanan, E.; Khan, F. A.; Chem. Rev. 2000, 100, 3065; (b) Ma, S.; Li, L. Synlett 2001, 8, 1206; (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (d) Ma, S.; Zhao, S. Org. Lett. 2000, 16, 2495.
    • (1998) J. Org. Chem. , vol.63 , pp. 6387
    • Ma, S.1    Shi, Z.2
  • 6
    • 0000244357 scopus 로고    scopus 로고
    • For the reaction of functionalized allenes, see: (a) Zimmer, R.; Dinesh, U.; Nandanan, E.; Khan, F. A.; Chem. Rev. 2000, 100, 3065; (b) Ma, S.; Li, L. Synlett 2001, 8, 1206; (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387; (d) Ma, S.; Zhao, S. Org. Lett. 2000, 16, 2495.
    • (2000) Org. Lett. , vol.16 , pp. 2495
    • Ma, S.1    Zhao, S.2
  • 22
    • 0025374143 scopus 로고
    • For the synthesis of optically active 2,3-allenols via the reaction of chiral allenylic or propargylic boron or tin reagents with aldehydes, see: (a) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878; (b) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130; (c) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125; (d) Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, K. J.-Y. Angew. Chem. 1998, 110, 2504; Angew. Chem., Int. Ed. 1998, 37, 2392.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 878
    • Corey, E.J.1    Yu, C.-M.2    Lee, D.-H.3
  • 23
    • 0001308870 scopus 로고
    • For the synthesis of optically active 2,3-allenols via the reaction of chiral allenylic or propargylic boron or tin reagents with aldehydes, see: (a) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878; (b) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130; (c) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125; (d) Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, K. J.-Y. Angew. Chem. 1998, 110, 2504; Angew. Chem., Int. Ed. 1998, 37, 2392.
    • (1995) J. Org. Chem. , vol.60 , pp. 8130
    • Brown, H.C.1    Khire, U.R.2    Narla, G.3
  • 24
    • 0029896271 scopus 로고    scopus 로고
    • For the synthesis of optically active 2,3-allenols via the reaction of chiral allenylic or propargylic boron or tin reagents with aldehydes, see: (a) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878; (b) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130; (c) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125; (d) Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, K. J.-Y. Angew. Chem. 1998, 110, 2504; Angew. Chem., Int. Ed. 1998, 37, 2392.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4125
    • Kulkarni, S.V.1    Brown, H.C.2
  • 25
    • 0000424026 scopus 로고    scopus 로고
    • For the synthesis of optically active 2,3-allenols via the reaction of chiral allenylic or propargylic boron or tin reagents with aldehydes, see: (a) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878; (b) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130; (c) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125; (d) Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, K. J.-Y. Angew. Chem. 1998, 110, 2504; Angew. Chem., Int. Ed. 1998, 37, 2392.
    • (1998) Angew. Chem. , vol.110 , pp. 2504
    • Yu, C.-M.1    Yoon, S.-K.2    Baek, K.3    Lee, K.J.-Y.4
  • 26
    • 0032544714 scopus 로고    scopus 로고
    • For the synthesis of optically active 2,3-allenols via the reaction of chiral allenylic or propargylic boron or tin reagents with aldehydes, see: (a) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878; (b) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130; (c) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125; (d) Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, K. J.-Y. Angew. Chem. 1998, 110, 2504; Angew. Chem., Int. Ed. 1998, 37, 2392.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2392
  • 27
    • 0003623760 scopus 로고
    • Academic Press Robinson, C. H.; Covey, D. F. in Ref. 1b, part 1, p. 451
    • Landor S.R. The Chemistry of the Allenes. 1-3:1982;Academic Press, New York, Robinson, C. H.; Covey, D. F. in Ref. 1b, part 1, p. 451.
    • (1982) The Chemistry of the Allenes , vol.13
    • Landor, S.R.1
  • 31
    • 84863240389 scopus 로고
    • For efficient kinetic resolutions of chiral allenes, see: (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 7434; (b) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129; (c) Ramaswamy, S.; Hui, R. A. H.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1986, 1545. Konegawa, T.; Ohtsuka, Y.; Ikeda, H.; Sugai, T.; Ohata, H. Synlett 1997, 1297.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7434
    • Burgess, K.1    Jennings, L.D.2
  • 32
    • 0001364513 scopus 로고
    • For efficient kinetic resolutions of chiral allenes, see: (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 7434; (b) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129; (c) Ramaswamy, S.; Hui, R. A. H.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1986, 1545. Konegawa, T.; Ohtsuka, Y.; Ikeda, H.; Sugai, T.; Ohata, H. Synlett 1997, 1297.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6129
    • Burgess, K.1    Jennings, L.D.2
  • 33
    • 37049066862 scopus 로고
    • For efficient kinetic resolutions of chiral allenes, see: (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 7434; (b) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129; (c) Ramaswamy, S.; Hui, R. A. H.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1986, 1545. Konegawa, T.; Ohtsuka, Y.; Ikeda, H.; Sugai, T.; Ohata, H. Synlett 1997, 1297.
    • (1986) J. Chem. Soc., Chem. Commun. , pp. 1545
    • Ramaswamy, S.1    Hui, R.A.H.2    Jones, J.B.3
  • 34
    • 0013549779 scopus 로고    scopus 로고
    • For efficient kinetic resolutions of chiral allenes, see: (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 7434; (b) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129; (c) Ramaswamy, S.; Hui, R. A. H.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1986, 1545. Konegawa, T.; Ohtsuka, Y.; Ikeda, H.; Sugai, T.; Ohata, H. Synlett 1997, 1297.
    • (1997) Synlett , pp. 1297
    • Konegawa, T.1    Ohtsuka, Y.2    Ikeda, H.3    Sugai, T.4    Ohata, H.5
  • 39
    • 9644285669 scopus 로고
    • For some seminal papers of Sonogarshira coupling reactions, see: (a) Sonogarshira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; (b) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167; (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109; (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977; (e) Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449; (f) Lin, S. Y.; Sheng, H. Y.; Huang, Y. Z. Synthesis 1991, 235.
    • (1975) Tetrahedron Lett. , pp. 4467
    • Sonogarshira, K.1    Tohda, Y.2    Hagihara, N.3
  • 40
    • 0000895709 scopus 로고
    • For some seminal papers of Sonogarshira coupling reactions, see: (a) Sonogarshira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; (b) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167; (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109; (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977; (e) Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449; (f) Lin, S. Y.; Sheng, H. Y.; Huang, Y. Z. Synthesis 1991, 235.
    • (1993) J. Organomet. Chem. , vol.457 , pp. 167
    • Hegedus, L.S.1
  • 41
    • 0026052526 scopus 로고
    • For some seminal papers of Sonogarshira coupling reactions, see: (a) Sonogarshira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; (b) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167; (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109; (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977; (e) Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449; (f) Lin, S. Y.; Sheng, H. Y.; Huang, Y. Z. Synthesis 1991, 235.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6109
    • Alami, M.1    Linstrumelle, G.2
  • 42
    • 0025866075 scopus 로고
    • For some seminal papers of Sonogarshira coupling reactions, see: (a) Sonogarshira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; (b) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167; (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109; (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977; (e) Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449; (f) Lin, S. Y.; Sheng, H. Y.; Huang, Y. Z. Synthesis 1991, 235.
    • (1991) Synth. Commun. , vol.21 , pp. 977
    • Wityak, J.1    Chan, J.B.2
  • 43
    • 0026071460 scopus 로고
    • For some seminal papers of Sonogarshira coupling reactions, see: (a) Sonogarshira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; (b) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167; (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109; (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977; (e) Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449; (f) Lin, S. Y.; Sheng, H. Y.; Huang, Y. Z. Synthesis 1991, 235.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1449
    • Bruckner, R.1    Scheuplein, S.W.2    Suffert, J.3
  • 44
    • 0026032479 scopus 로고
    • For some seminal papers of Sonogarshira coupling reactions, see: (a) Sonogarshira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467; (b) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167; (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109; (d) Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977; (e) Bruckner, R.; Scheuplein, S. W.; Suffert, J. Tetrahedron Lett. 1991, 32, 1449; (f) Lin, S. Y.; Sheng, H. Y.; Huang, Y. Z. Synthesis 1991, 235.
    • (1991) Synthesis , pp. 235
    • Lin, S.Y.1    Sheng, H.Y.2    Huang, Y.Z.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.