메뉴 건너뛰기




Volumn 65, Issue 6, 2000, Pages 1601-1614

Stereoselective synthesis of (Z)- and (E)-allylic silanes by copper- mediated substitution reactions of allylic carbamates with grignard reagents

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; COPPER; SILANE DERIVATIVE;

EID: 0034708811     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991312r     Document Type: Article
Times cited : (49)

References (76)
  • 1
    • 0343778881 scopus 로고
    • For a review discussing the use of chiral allylsilanes in synthesis, see: Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316.
    • (1995) Chem. Rev. , vol.95 , pp. 1293-1316
    • Masse, C.E.1    Panek, J.S.2
  • 4
    • 17744413360 scopus 로고    scopus 로고
    • For a review on [3 + 2] annulation reactions of allyltriisopropylsilane, see: Knölker, H.-J. J. Prakt. Chem. 1997, 339, 304-314.
    • (1997) J. Prakt. Chem. , vol.339 , pp. 304-314
    • Knölker, H.-J.1
  • 13
    • 0025029262 scopus 로고
    • For a review of methods for the synthesis of allylsilanes, see: Sarkar, T. K. Synthesis 1990, 969-983. Sarkar, T. K. Synthesis 1990, 1101-1111.
    • (1990) Synthesis , pp. 969-983
    • Sarkar, T.K.1
  • 14
    • 0025690403 scopus 로고
    • For a review of methods for the synthesis of allylsilanes, see: Sarkar, T. K. Synthesis 1990, 969-983. Sarkar, T. K. Synthesis 1990, 1101-1111.
    • (1990) Synthesis , pp. 1101-1111
    • Sarkar, T.K.1
  • 15
    • 0000047923 scopus 로고    scopus 로고
    • For a method to prepare enantiomerically enriched (E)-allylic silanes, see: Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061-3062.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3061-3062
    • Suginome, M.1    Matsumoto, A.2    Ito, Y.3
  • 32
    • 0343883417 scopus 로고    scopus 로고
    • note
    • Pivalate esters have been employed in the copper-catalyzed allylic substitution reaction to disfavor attack of the Grignard reagent on the carbonyl.
  • 34
    • 0343011975 scopus 로고    scopus 로고
    • note
    • 1H NMR coupling constants, by comparison of spectral data to reported data, or by comparison to reference materials.
  • 36
    • 85026923637 scopus 로고    scopus 로고
    • This reaction sequence was adapted from that reported for the synthesis of 3-(tert-butyldimethylsilyl)-2-propyn-1-ol: Myers, A. G.; Zheng, B. Org. Synth. 1998, 76, 178-188.
    • (1998) Org. Synth. , vol.76 , pp. 178-188
    • Myers, A.G.1    Zheng, B.2
  • 45
    • 0011492479 scopus 로고
    • Wiley: New York
    • Voskuil, W.; Arsens, J. F. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. V, pp 211-214.
    • (1963) Organic Syntheses , vol.5 COLLECT. VOL. , pp. 211-214
    • Voskuil, W.1    Arsens, J.F.2
  • 46
    • 0000995562 scopus 로고
    • For the copper-catalyzed reactions of terminal and cyclic allylic phosphates and chlorides with titanate reagents, see: Arai, M.; Nakamura, E.; Lipshutz, B. H. J. Org. Chem. 1991, 56, 5489-5491. Arai, M.; Lipshutz, B. H.; Nakamura, E. Tetrahedron 1992, 48, 5709- 5718.
    • (1991) J. Org. Chem. , vol.56 , pp. 5489-5491
    • Arai, M.1    Nakamura, E.2    Lipshutz, B.H.3
  • 47
    • 0001091801 scopus 로고
    • For the copper-catalyzed reactions of terminal and cyclic allylic phosphates and chlorides with titanate reagents, see: Arai, M.; Nakamura, E.; Lipshutz, B. H. J. Org. Chem. 1991, 56, 5489-5491. Arai, M.; Lipshutz, B. H.; Nakamura, E. Tetrahedron 1992, 48, 5709-5718.
    • (1992) Tetrahedron , vol.48 , pp. 5709-5718
    • Arai, M.1    Lipshutz, B.H.2    Nakamura, E.3
  • 48
    • 0013506629 scopus 로고
    • For the copper-catalyzed reactions of allylic chlorides and phosphates with organozinc reagents, see: (a) Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5155-5156. (b) Nakamura, E.; Sekiya, K.; Arai, M.; Aoki, S. J. Am. Chem. Soc. 1989, 111, 3091-3093. (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445- 1453.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5155-5156
    • Sekiya, K.1    Nakamura, E.2
  • 49
    • 0000592991 scopus 로고
    • For the copper-catalyzed reactions of allylic chlorides and phosphates with organozinc reagents, see: (a) Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5155-5156. (b) Nakamura, E.; Sekiya, K.; Arai, M.; Aoki, S. J. Am. Chem. Soc. 1989, 111, 3091-3093. (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445- 1453.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3091-3093
    • Nakamura, E.1    Sekiya, K.2    Arai, M.3    Aoki, S.4
  • 50
    • 0000358709 scopus 로고
    • For the copper-catalyzed reactions of allylic chlorides and phosphates with organozinc reagents, see: (a) Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5155-5156. (b) Nakamura, E.; Sekiya, K.; Arai, M.; Aoki, S. J. Am. Chem. Soc. 1989, 111, 3091-3093. (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453.
    • (1991) J. Org. Chem. , vol.56 , pp. 1445-1453
    • Zhu, L.1    Wehmeyer, R.M.2    Rieke, R.D.3
  • 55
    • 0000449963 scopus 로고
    • Kitano's procedure for Sharpless kinetic resolution of γ-silyl allylic alcohols was followed: Kitano, Y.; Matsumoto, T.; Sato, F. Tetrahedron 1988, 44, 4073-4086.
    • (1988) Tetrahedron , vol.44 , pp. 4073-4086
    • Kitano, Y.1    Matsumoto, T.2    Sato, F.3
  • 62
    • 0026663693 scopus 로고
    • For a review of methods available for the enantioselective reduction of ketones, see: Singh, V. K. Synthesis 1992, 605-617.
    • (1992) Synthesis , pp. 605-617
    • Singh, V.K.1
  • 65
    • 33645897192 scopus 로고
    • For a discussion of allylic strain, see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
    • (1989) Chem. Rev. , vol.89 , pp. 1841-1860
    • Hoffmann, R.W.1
  • 75
    • 0343011973 scopus 로고    scopus 로고
    • note
    • Details are provided as Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.