Tetrakis[(4S)-4-phenyloxazolidin-2-one]dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations
✍ Scribed by Michael P. Doyle; William R. Winchester; Marina N. Protopopova; Paul Müller; Gérald Bernardinelli; Doina Ene; Sharokh Motallebi
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- German
- Weight
- 602 KB
- Volume
- 76
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
The synthesis and X-ray structure of the binucledr complex tetrakis[(4S)-4-phenyloxazolidin-2-one]dirhodium(I1) ([Rh2{(4S)-phox},]) are reported. Structure-selectivity comparisons are made for typical metal carbcne transformations, such as inter-and intramolecular cyclopropane formation, intermolecular cyclopropene formation and intramolecular C-H insertions of diazoacetates and diazoacetamides. The enantioselectivity achieved in the [Rh2((4S)-phox],]-catalyzed reactions is intermediate between that of [Rh2((5S)-mepy},] and [Rh2((4R)-bnox},], which were described previousiy (mepy = methyl S-oxopyrrolidine-2-carboxylate; bnox = 4beuzyloxazolidin-2-one). In contrast to other catalyzed intermolecular cyclopropane formations, those using [Rh2{(4S)-phox},] result preferentially in formation of the cix-cyclopropane.
') These ligands were formerly called 'methyl 2-pyrrolidone-5-carboxylates', e.g. Rh2(5S-MEPY),.