N-H insertion reactions of rhodium carbenoids. Part 1. Preparation of  -amino acid and  -aminophosphonic acid derivatives.

E. Aller, R.T. Buck, M.J. Drysdale, L. Ferris, David Haigh, C.J. Moody, N.D. Pearson, J.B. Sanghera

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Abstract

Rh(II) acetate-catalyzed decompn. of diazophenylacetates PhC(N2)CO2Me 1 and PhC(N2)CO2R* 3 [R*OH = (-)-borneol, (+)-menthol, (-)-8-phenylmenthol] in the presence of a range of N-H compds. results in an N-H insertion reaction of the intermediate carbenoids and formation of N-substituted phenylglycine derivs. PhCH(NR1R2)CO2Me 2 [R1 = R2 = Et; R1 = 4-MeOC6H4, COCH2CHMe2, CO2CH2Ph, (S)-CH(CO2Me)CH2Ph, (S)-CHMePh, R2 = H; 64-83% yields] and PhCH(NR1R2)CO2R* 4 (R1 = R2 = Et; R1 = COMe, CO2Me, R2 = H; same R*; 37-71% yields). The corresponding reactions of di-Me ?-diazobenzylphosphonate PhC(N2)P(O)(OMe)2 5 with primary amines constitute a simple route to aminophosphonates PhCH(NHR)P(O)(OMe)2 6 (R = COMe, COEt, CO2CH2Ph, CO2CMe3, 4-ClC6H4, 4-MeC6H4, 4-MeOC6H4; 13-96% yields).
Original languageEnglish
Pages (from-to)2879-2884
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Volume-
Publication statusPublished - 1996

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    Aller, E., Buck, R. T., Drysdale, M. J., Ferris, L., Haigh, D., Moody, C. J., Pearson, N. D., & Sanghera, J. B. (1996). N-H insertion reactions of rhodium carbenoids. Part 1. Preparation of  -amino acid and  -aminophosphonic acid derivatives. Journal of the Chemical Society - Perkin Transactions 1, -, 2879-2884.