Scientific article

Tetrakis[(4S)-4-phenyloxazolidin-2-one]dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations

Published inHelvetica chimica acta, vol. 76, no. 6, p. 2227-2235
Publication date1993

The synthesis and X-ray structure of the binuclear complex tetrakis[(4S)-4-phenyloxazolidin-2-one]-dirhodium(II) ([Rh2{(4S)-phox}4]) are reported. Structure-selectivity comparisons are made for typical metal carbene 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}4]-catalyzed reactions is intermediate between that of [Rh2{(5S)-mepy}4] and [Rh2{(4R)-bnox}4], which were described previously (mepy = methyl 5-oxopyrrolidine-2-carboxylate; bnox = 4-benzyloxazolidin-2-one). In contrast to other catalyzed intermolecular cyclopropane formations, those using [Rh2{(4S)-phox}4] result preferentially in formation of the cis-cyclopropane.

Citation (ISO format)
DOYLE, Michael P. et al. Tetrakis[(4<i>S</i>)-4-phenyloxazolidin-2-one]dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations. In: Helvetica chimica acta, 1993, vol. 76, n° 6, p. 2227–2235. doi: 10.1002/hlca.19930760606
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Article (Published version)
ISSN of the journal0018-019X

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