Generation of a reducing reagent from Copper(I) salt and hydrosilane. New practical method for conjugate reduction

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8887-8890

  Ito, Hajime ^a   Ishizuka, Tomoko ^a   Arimoto, Kikuo ^a   Miura, Katsukiyo ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; CYCLOHEXANE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0030733481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10326-4     Document Type: Article

References (14)

1. Studies on Organosilicon Chemistry. No. 138.
2. Schlosser, M. Organometallic in Synthesis: A Manual John Wiley & Suns: New York 1996.
3. (a) Whitesides, G. M.; Filippo, J. S.; Stredronsky, E. R.; Casey, C. P. J. Am. Chem. Soc. 1969, 91, 6542.
4. (b) Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem., 1977, 42, 3180.
5. (c) Tsuda, T.; Satomi, H.; Hayashi, T. and Saegusa, T. J. Org. Chem., 1987, 52, 439.
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7. (e) Lipshutz, B. H.; Ung, C. S.; Sengupta S. Synlett. 1989, 1, 64.
8. Copper-catalyzed hydrosilylation of isocyanide was reported. Saegusa, T.; Ito, Y.; Kobayashi, S.; Hirota, K. J. Am. Chem. Soc. 1967, 89, 2240.
9. (a) Ito, H.; Arimoto, K.; Sensui, H.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977.
10. (b) Ito, H.; Sensui, H.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639.
11. Recently Hiyama et al. reported the oxidative coupling reaction of fluorinated organosilanes mediated by a copper(I) salt Ikegashira, K.; Nishihara Y.; Hirabayashi, K.; Mon, A.; Hiyama, T.Chem. Commun. 1997, 1039.
12. 29Si NMR measurements of the reaction mixture and chlorodimethylphenylsilane 2a were carried out under nitrogen in DMI. The chemical shifts were calibrated by tetramethylsilane as an internal standard (δ 0.0).
13. Hydrogenation of 3g with a Pd/C catalyst gave a stereomixture of 96:4 (cis : trans).
14. Boudjouk, P.; Kloos, S.; Rajkumar, A. B. J. Organomet. Chem. 1993, 443, C41-C43.