Highly Stereoselective 1,3-Dipolar Cycloaddition of Nitrones to (Nitrile)2PtII Species Furnishing Diastereomerically Pure 2,3-Dihydro-1,2,4-oxadiazole Ligands

被引：21

作者：

Bokach, Nadezhda A. ^{[1
]}

Balova, Irina A. ^{[1
]}

Haukka, Matti ^{[2
]}

Kukushkin, Vadim Yu ^{[1
,3
]}

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] Univ Eastern Finland, Dept Chem, FI-80101 Joensuu, Finland

[3] Russian Acad Sci, Inst Macromol Cpds, St Petersburg 199004, Russia

来源：

ORGANOMETALLICS | 2011年 / 30卷 / 03期

关键词：

PLATINUM(II) NITRILE COMPLEXES; X-RAY; LEWIS-ACID; BOUND ORGANONITRILES; TETRAZOLE FORMATION; CRYSTAL-STRUCTURES; SIMPLE-MODEL; KEY STEP; ROUTE; SUBSTITUENT;

D O I：

10.1021/om100957b

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diastereomerically pure platinum(II) complexes 4-9 bearing tetrahydro-5,8-methanocyclohexa-[3',2':4,5][1,3]oxazolo[3,2-b][1,2,4]oxadiazole ligands were generated under mild conditions (CH2Cl2, 20-25 degrees C, 24 h) by an intermolecular Pt-II-mediated 1,3-dipolar cycloaddition between enantiomerically pure camphor-derived oxazoline-N-oxides and the coordinated nitriles in the complexes trans-[PtCl2(R'CN)(2)] (R' = Et, Ph, NMe2). These species were characterized by elemental analyses (C, H, N), high-resolution ESI+-MS, IR, H-1 and C-13 NM R spectroscopies, and also X-ray diffraction (for 5, 7, 8 center dot CHCl3, and 9 center dot Me2CO). Free heterocycles 10-13 were liberated as single stereoisomers from the (2,3-dihydro-1,2,4-oxadiazole)(2) Pt-II complexes (R = Et, Ph) by treatment with excess NaCN and were characterized by high-resolution ESI+-MS and H-1 and C-13 NMR spectroscopies.

引用

页码：595 / 602

页数：8

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