Publication Type Journal Article
Title Metal-mediated coupling of amino acid esters with isocyanides leading to new chiral acyclic aminocarbene complexes
Authors Tatyana B. Anisimova M. Fátima C. Guedes da Silva V. Yu. Kukushkin Armando J.L. Pombeiro K. Luzyanin
Groups CCC
Journal DALTON TRANSACTIONS
Year 2014
Month November
Volume 43
Number 42
Pages 15861-15871
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)=NHR1)(1) (R-1 = Xyl 9, 2-Cl-6-Me-C6H3 10) or cis-[PdCl2(CNR1)\C(ProOtBu)=NHR1\] (R-1 = Xyl 11, 2-CE-6-Me-C6H3 12, Cy 13, tBu 14, 2-naphthyl 15) in good to excellent isolated yields (75-94\%). The corresponding reaction between trans-[Pdl(2)(CNR1)(2)] (6) and 8 brings about the formation of trans-[Pd1(2)(CNCy)\C(ProOtBu) NHCy)1 (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 (H-1, C-13(H)) and 2D (H-1,H-1 -COSY, H-1,C-13-HMQC/1H,13C-HSQC, 1H,13C-HMBC) NM R spectroscopic techniques, and by single-crystal X-ray diffraction (for 9, 11-13, and 16).
DOI http://dx.doi.org/10.1039/c4dt01917b
ISBN
Publisher ROYAL SOC CHEMISTRY
Book Title
ISSN 1477-9226
EISSN 1477-9234
Conference Name
Bibtex ID ISI:000343958900024
Observations
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