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Volumn 13, Issue 22, 2002, Pages 2449-2452

Selective synthesis of optically active allenic and homopropargylic alcohols from propargyl chloride

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALLENYLTRICHLOROSILANE; OXIDE; PROPARGYL CHLORIDE; PROPARGYLTRICHLOROSILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037073344     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00640-7     Document Type: Article
Times cited : (82)

References (23)
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    • For catalytic enantioselective homopropargylation, see: (a) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324; (b) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K. Chem. Commun. 1997, 763-764; (c) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889-890; (d) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095-12096; (e) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Tino, R.; Umani-Ronchi, A. Tetrahedron: Asymmetry 2001, 12, 1063-1069; (f) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200.
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    • For catalytic enantioselective homopropargylation, see: (a) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324; (b) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K. Chem. Commun. 1997, 763-764; (c) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889-890; (d) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095-12096; (e) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Tino, R.; Umani-Ronchi, A. Tetrahedron: Asymmetry 2001, 12, 1063-1069; (f) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200.
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    • For catalytic enantioselective homopropargylation, see: (a) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324; (b) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K. Chem. Commun. 1997, 763-764; (c) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung, W.-H. Synlett 1997, 889-890; (d) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095-12096; (e) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Tino, R.; Umani-Ronchi, A. Tetrahedron: Asymmetry 2001, 12, 1063-1069; (f) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200.
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    • note
    • 4,6.
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    • For enantioselective allylation of aldehydes with allyltrichlorosilane catalyzed by chiral Lewis base other than N-oxide, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163; (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150; (c) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770.
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    • For enantioselective allylation of aldehydes with allyltrichlorosilane catalyzed by chiral Lewis base other than N-oxide, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163; (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150; (c) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770.
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    • 0032580431 scopus 로고    scopus 로고
    • For enantioselective allylation of aldehydes with allyltrichlorosilane catalyzed by chiral Lewis base other than N-oxide, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163; (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149-5150; (c) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770.
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    • . Very recently, Hayashi and co-workers reported a highly enantioselective allylation of aldehydes with allyltrichlorosilane in the presence of a chiral N-oxide with extremely high catalytic activity (0.01 mol% loading). Shimada T., Kina A., Ikeda S., Hayashi T. Org. Lett. 4:2002;2799-2801.
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    • note
    • When a 1:1 mixture of allenyl- and propargyltrichlorosilane purified by distillation was used, the reaction with benzaldehyde under otherwise identical conditions afforded a 1:1 mixture of homopropargylic and allenic alcohols in 48 and 52% e.e., respectively. These results suggest that the presence of nickel bis(acetylacetate) and cuprous chloride have no detrimental influence on enantioselection in these reactions.


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