Rhodium catalysed reactions of silylated diazoacetates: Stereoselective synthesis of α-silylated γ-lactones via C-H insertion

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 6077-6080

  Marsden, Stephen P ^a   Pang, Wai Kit ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Carbenes and carbenoids; Diazo compounds; Lactones; Silicon and compounds

Indexed keywords

GAMMA LACTONE DERIVATIVE; RHODIUM;

ARTICLE; CARBOXYLATION; CATALYST; CHEMICAL ANALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032514443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01252-0     Document Type: Article

References (16)

1. 1. Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankina, N. S. Tetrahedron 1988, 44, 2675
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3. 3. Ager, D. J. Org. React. 1990, 38, 1
4. 4. We have recently described the C-H insertion reactions of silicon tethered silyldiazoacetates, based upon the results described herein: Kablean, S. N; Marsden, S. P.; Craig, A. M. Tetrahedron Lett. 1998, in press
5. 5. Schöllkopf, U.; Hoppe, D.; Rieber, N.; Jacobi, V. Liebigs Ann. Chem. 1969, 730, 1
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10. 10. Prepared by a modified House procedure: Corey, E. J.; Myers, A. G. Tetrahedron Lett. 1984, 25, 3559
11. 11. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958
12. 11 In compound 5, the corresponding J values are 10.4 and 11.0Hz.
13. 13. The lactones were reduced to 1,4-diols using DIBAL-H, then converted to their crystalline bis-(3,5-dinitrobenzoate) esters. We thank Professor D. J. Williams and Dr A. J. P. White of this department for determining these structures, details of which will be published elsewhere.
14. 14. The effects of chiral rhodium catalysts upon diastereoselection in C-H insertion reactions have been discussed: Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837
15. 15. The relevant coupling constants are shown below. The signals for H-4 and H-5 are obscured in the spectrum of 6b, hence no J value is shown for this compound. (equation presented)
16. 16. Pirrung, M. C.; Morehead, A. T. J. Am. Chem. Soc. 1994, 116, 8991 Tetrahedron Letters 39 (1998) 6081-6082