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Volumn 61, Issue 18, 1996, Pages 6108-6113

Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides

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EID: 0000803525     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960244v     Document Type: Article
Times cited : (89)

References (41)
  • 2
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    • and references cited therein
    • For recent general reviews in this area, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1 and references cited therein. (b) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (c). Simpkins, N. S. Chem. Ind. 1988, 387.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 1
    • Cox, P.J.1    Simpkins, N.S.2
  • 3
    • 0002350886 scopus 로고
    • For recent general reviews in this area, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1 and references cited therein. (b) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (c). Simpkins, N. S. Chem. Ind. 1988, 387.
    • (1990) Chem. Soc. Rev. , vol.19 , pp. 1
    • Ward, R.S.1
  • 4
    • 0002979706 scopus 로고
    • For recent general reviews in this area, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1 and references cited therein. (b) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (c). Simpkins, N. S. Chem. Ind. 1988, 387.
    • (1988) Chem. Ind. , pp. 387
    • Simpkins, N.S.1
  • 14
    • 0001117008 scopus 로고
    • For recent reviews, see: (a) Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345. (b) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semelhack, M. F., Eds.; Pergamon Press: Oxford; 1991; Vol. 1, p 733.
    • (1983) Org. React. , vol.29 , pp. 345
    • Crandall, J.K.1    Apparu, M.2
  • 15
    • 0001312924 scopus 로고
    • Trost, B. M., Fleming, I., Semelhack, M. F., Eds.; Pergamon Press: Oxford
    • For recent reviews, see: (a) Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345. (b) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semelhack, M. F., Eds.; Pergamon Press: Oxford; 1991; Vol. 1, p 733.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 733
    • Rickborn, B.1
  • 17
    • 3643057482 scopus 로고    scopus 로고
    • note
    • We thank one of the referees for this suggestion to explain the lower enantioselectivity with the ligand (R)-6c.
  • 19
    • 33751385836 scopus 로고
    • For the effect of LiCl on enantioselective deprotonation of cyclic ketones, see: (a) Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. (b) Majewski, M.; Lazny, R.; Nowak, P. Tetrahedron Lett. 1995, 36, 5465.
    • (1993) J. Org. Chem. , vol.58 , pp. 533
    • Bunn, B.J.1    Simpkins, N.S.2
  • 20
    • 85047673542 scopus 로고
    • For the effect of LiCl on enantioselective deprotonation of cyclic ketones, see: (a) Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533. (b) Majewski, M.; Lazny, R.; Nowak, P. Tetrahedron Lett. 1995, 36, 5465.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5465
    • Majewski, M.1    Lazny, R.2    Nowak, P.3
  • 21
    • 2342641717 scopus 로고
    • Asymmetric Synthesis using Chiral Bases
    • Chizhov, O., Ed.; Blackwell Scientific Publication: London
    • Koga, K. Asymmetric Synthesis using Chiral Bases. In Organic Synthesis: Modern Trends; Chizhov, O., Ed.; Blackwell Scientific Publication: London, 1987; p 285.
    • (1987) Organic Synthesis: Modern Trends , pp. 285
    • Koga, K.1
  • 22
    • 3643058607 scopus 로고    scopus 로고
    • note
    • We thank Professor Koga for providing specific rotation data of 5a.
  • 32
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    • Recently, Asami reconfirmed his previous results of 90% ee in the deprotonation of the epoxide 15a with a proline-based base. For reference, see: Asami, M.; Inoue, S. Tetrahedron 1995, 51, 11725.
    • (1995) Tetrahedron , vol.51 , pp. 11725
    • Asami, M.1    Inoue, S.2
  • 33
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    • note
    • The work has been communicated in preliminary form, see ref 6a.
  • 38
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    • (d) For detailed calculations which suggest little difference in proton affinity between dialkyl ethers and sterically analogous alkyl silyl ethers, see: Blake, J. F.; Jorgensen, W. L. J. Org. Chem. 1991, 56, 6052.
    • (1991) J. Org. Chem. , vol.56 , pp. 6052
    • Blake, J.F.1    Jorgensen, W.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.