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Issue 42, 2014
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Metal-mediated coupling of amino acid esters with isocyanides leading to new chiral acyclic aminocarbene complexes

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Abstract

Metal-mediated coupling between equimolar amounts of cis-[PdCl2(CNR1)2] (1–5) and the amino acid esters L-HTyrOMe (7) or L-HProOtBu (8) proceeds at 40 °C in chloroform over ca. 6 h. The subsequent workup affords the complexes cis-[PdCl2(CNR1){C(TyrOMe)[double bond, length as m-dash]NHR1}] (R1 = Xyl 9, 2-Cl-6-Me-C6H310) or cis-[PdCl2(CNR1){C(ProOtBu)[double bond, length as m-dash]NHR1}] (R1 = Xyl 11, 2-Cl-6-Me-C6H312, Cy 13, tBu 14, 2-naphthyl 15) in good to excellent isolated yields (75–94%). The corresponding reaction between trans-[PdI2(CNR1)2] (6) and 8 brings about the formation of trans-[PdI2(CNCy){C(ProOtBu)[double bond, length as m-dash]NHCy}] (16, 76% isolated yield). The reaction of 6 with 7 proceeds non-selectively giving a broad mixture of products. Complexes 9–16 were characterized by elemental analyses (C, H, N), ESI+/−-MS, IR, 1D (1H, 13C{H}) and 2D (1H,1H-COSY, 1H,13C-HMQC/1H,13C-HSQC, 1H,13C-HMBC) NMR spectroscopic techniques, and by single-crystal X-ray diffraction (for 9, 11–13, and 16).

Graphical abstract: Metal-mediated coupling of amino acid esters with isocyanides leading to new chiral acyclic aminocarbene complexes

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Publication details

The article was received on 25 Jun 2014, accepted on 13 Aug 2014 and first published on 14 Aug 2014


Article type: Paper
DOI: 10.1039/C4DT01917B
Citation: Dalton Trans., 2014,43, 15861-15871
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    Metal-mediated coupling of amino acid esters with isocyanides leading to new chiral acyclic aminocarbene complexes

    T. B. Anisimova, M. F. C. Guedes da Silva, V. Yu. Kukushkin, A. J. L. Pombeiro and K. V. Luzyanin, Dalton Trans., 2014, 43, 15861
    DOI: 10.1039/C4DT01917B

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