No.140
Horner-Wadsworth-Emmons Reagents for E and Z-Selective Synthesis
| D3708 | Diethyl (N-Methoxy-N-methylcarbamoylmethyl)phosphonate (1) |
1g 5g |
| D3709 | Diphenyl (N-Methoxy-N-methylcarbamoylmethyl)phosphonate (2) |
1g 5g |
Horner-Wadsworth-Emmons reagent 1 react with aldehydes and ketones to give corresponding E-α,β-unsaturated N-methoxy-N-methylamides.1) The presence of the Weinreb-Nahm amide, which can be transformed to aldehydes and ketones, makes 1 a useful reagent as a bifunctional building block.2) In contrast, Ando reported an useful Z selective olefination using Horner-Wadsworth-Emmons reagent (Ando-type reagent) 2.3) Synthetic applications of 2 are being studying.4)
References
1) Horner-Wadsworth-Emmons reagent for E-selective synthesis
a) J.-M. Nuzillard, A. Boumendjel, G. Massiot, Tetrahedron Lett. 1989, 30, 3779[DOI]. b) D. F. Netz, J. L. Seidel, Tetrahedron Lett. 1992, 33, 1957[DOI].
2) E-selective synthetic applications
a) L. C. Dias, V. G. Correia, F. G. Finelli, Tetrahedron Lett. 2007, 48, 7683[DOI]. b) C.-D. Lu, A. Zakarian, Org. Lett. 2007, 9, 3161[DOI]. c) P. Etayo, R. Badorrey, M. D. Díaz-de-Villegas, J. A. Gálvez, J. Org. Chem. 2007, 72, 1005[DOI].
3) Horner-Wadsworth-Emmons (Ando-type) reagent for Z-selective synthesis
K. Ando, Synlett 2001, 1272[DOI].
4) Z-selective synthetic applications
a) S. Kojima, T. Hidaka, A. Yamakawa, Chem. Lett. 2005, 34, 470[DOI]. b) T. Momose, N. Hama, C. Higashino, H. Sato, N. Chida, Tetrahedron Lett. 2008, 49, 1376[DOI].
a) J.-M. Nuzillard, A. Boumendjel, G. Massiot, Tetrahedron Lett. 1989, 30, 3779[DOI]. b) D. F. Netz, J. L. Seidel, Tetrahedron Lett. 1992, 33, 1957[DOI].
2) E-selective synthetic applications
a) L. C. Dias, V. G. Correia, F. G. Finelli, Tetrahedron Lett. 2007, 48, 7683[DOI]. b) C.-D. Lu, A. Zakarian, Org. Lett. 2007, 9, 3161[DOI]. c) P. Etayo, R. Badorrey, M. D. Díaz-de-Villegas, J. A. Gálvez, J. Org. Chem. 2007, 72, 1005[DOI].
3) Horner-Wadsworth-Emmons (Ando-type) reagent for Z-selective synthesis
K. Ando, Synlett 2001, 1272[DOI].
4) Z-selective synthetic applications
a) S. Kojima, T. Hidaka, A. Yamakawa, Chem. Lett. 2005, 34, 470[DOI]. b) T. Momose, N. Hama, C. Higashino, H. Sato, N. Chida, Tetrahedron Lett. 2008, 49, 1376[DOI].
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