Abstract
Enantiomerically pure ( S)-2-(anilinomethyl)pyrrolidine ( S)- 2 was obtained from ( S)-proline using a modified four-step procedure in a total yield of 56%. Diamine ( S)- 2 was converted to diazaphospholidine ( S)- 1 using o TolP(NMe 2) 2. The enantiomeric purity of ligand ( S)- 1 and diamine ( S)- 2 was determined by 31P and 1H NMR spectroscopy, respectively, using a CN-palladacycle for their chiral derivatization. Direct cyclopalladation of ( S)- 1, using Pd(OAc) 2 in toluene under mild conditions regioselectively afforded the cyclopalladated complex with the (sp 2)C–Pd bond. The aromatic C–H bond activation was confirmed by NMR spectral data and X-ray diffraction study of the PPh 3 derivative of the new P ∗, C ∗, N ∗-chiral phosphapalladacycle.
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