Cu(I)-catalyzed enantioselective [2 + 2] cycloaddition of 1-methoxyallenylsilane with α-imino ester: Chiral synthesis of α,β-unsaturated acylsilanes

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3691-3693

  Akiyama, Takahiko ^a   Daidouji, Kazunori ^a   Fuchibe, Kohei ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMINO ACID; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; ENANTIOMER; ENANTIOSELECTIVITY; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; RING OPENING;

EID: 0142106416     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0353621     Document Type: Article

References (34)

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21. For enantioselective Cu(I)-catalyzed nucleophilic addition reaction with α-imino ester, see: Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yao, S.; Fang, X.; Jørgensen, K. A. Chem. Commun. 1998, 2547. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; W. J. Drury, I.; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
22. For enantioselective Cu(I)-catalyzed nucleophilic addition reaction with α-imino ester, see: Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yao, S.; Fang, X.; Jørgensen, K. A. Chem. Commun. 1998, 2547. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; W. J. Drury, I.; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
23. For enantioselective Cu(I)-catalyzed nucleophilic addition reaction with α-imino ester, see: Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yao, S.; Fang, X.; Jørgensen, K. A. Chem. Commun. 1998, 2547. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; W. J. Drury, I.; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
24. For enantioselective Cu(I)-catalyzed nucleophilic addition reaction with α-imino ester, see: Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yao, S.; Fang, X.; Jørgensen, K. A. Chem. Commun. 1998, 2547. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; W. J. Drury, I.; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
25. For enantioselective Cu(I)-catalyzed nucleophilic addition reaction with α-imino ester, see: Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yao, S.; Fang, X.; Jørgensen, K. A. Chem. Commun. 1998, 2547. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; W. J. Drury, I.; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
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31. We could not obtain 3 as crystals. All our attempts to determine the relative stereochemistry of 3 by NOE experiments failed.
32. CCDC 207580 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the Internet at http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
33. When the reaction was quenched under neutral conditions, both azetidine and acylsilane were obtained as a 1:1 mixture.
34. 2 was the sole identifiable product.