Carbenoid insertions into the silicon-hydrogen bond catalyzed by chiral copper (I) Schiff base complexes

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8947-8950

  Dakin, Les A ^a   Schaus, Scott E ^a   Jacobsen, Eric N ^a   Panek, James S ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ARYLACETIC ACID DERIVATIVE; AZO COMPOUND; CARBENOID; COPPER; SCHIFF BASE; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; HYDROGEN BOND; REACTION ANALYSIS;

EID: 0032480937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02013-9     Document Type: Article

References (16)

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2. (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316 and references cited therein. Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165-1166.
3. (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316 and references cited therein. Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165-1166.
4. 2. For a discussion regarding the limitations of the enolate based method of generating α-silyl carbonyl compounds and leading references see: Bagheri, V.; Doyle, M. P.; Taunton, J.; Claxton, E. E. J. Org. Chem. 1988, 53, 6158-6160.
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9. 4. (a) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5329.
10. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889-5892.
11. 5. Landais has demonstrated the use of achiral copper (II) complexes for the Si-H insertion process: Andrey, O.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron 1995, 51, 12083-12096.
12. 3Si to OH see: Fleming, I. Chemtracts Org. Chem. 1996, 9, 1-64. (formula presented)
13. 7. For a recent review, see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
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15. 9. The following results were obtained with Cu(I)-oxazoline and pybox complexes at -25° C: 2,2′-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] (61% ee), 2,2′-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] (61% ee), 2,2′-isopropylidenebis[(4S)-4-aminoindanol-2-oxazoline] (83% ee), di-tert-butylpybox (53% ee), diphenylpybox (49% ee).
16. 10. Palucki, M.; Finney, N. S.; Pospisil, P. J.; Guler, M. L.; Ishidia, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954.