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Diastereoselective Substitution of PR3 for CO in Carbohydrato- and Menthyloxycarbene Complexes of Manganese – Synthesis of Chiral-at-metal Carbene and Carbyne Complexes

Diastereoselective Substitution of PR3 for CO in Carbohydrato- and Menthyloxycarbene Complexes of Manganese – Synthesis of Chiral-at-metal Carbene and Carbyne Complexes

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FISCHER, Helmut, Joachim SCHLEU, 1996. Diastereoselective Substitution of PR3 for CO in Carbohydrato- and Menthyloxycarbene Complexes of Manganese – Synthesis of Chiral-at-metal Carbene and Carbyne Complexes. In: Chemische Berichte. 129(4), pp. 385-390. ISSN 0009-2940. eISSN 1099-0682. Available under: doi: 10.1002/cber.19961290404

@article{Fischer1996Diast-23078, title={Diastereoselective Substitution of PR3 for CO in Carbohydrato- and Menthyloxycarbene Complexes of Manganese – Synthesis of Chiral-at-metal Carbene and Carbyne Complexes}, year={1996}, doi={10.1002/cber.19961290404}, number={4}, volume={129}, issn={0009-2940}, journal={Chemische Berichte}, pages={385--390}, author={Fischer, Helmut and Schleu, Joachim} }

2013-06-19T08:26:17Z eng Diastereoselective Substitution of PR3 for CO in Carbohydrato- and Menthyloxycarbene Complexes of Manganese – Synthesis of Chiral-at-metal Carbene and Carbyne Complexes 2013-06-19T08:26:17Z Fischer, Helmut 1996 Schleu, Joachim Schleu, Joachim deposit-license Fischer, Helmut The substitution of PR3 (R = C6H4CH3-p, C6H4Cl-p, C6H11,OCH3) for a CO ligand in chiral carbohydratocarbene complexes [(η5-C5H5)(CO)2Mn[DOUBLE BOND]C(OR*)Ph] [OR* = α- (1α) and β-mannofuranosyl (1β), (–)-menthyloxy (9)] proceeds diastereoselectively. The diastereoselectivity depends on PR3 and on the OR* substituent and ranges from 12% de (R = OCH3) to 80% (R = C6H4CH3-p). In contrast, the reaction of 1β with P(OPh)3 is non-selective. The diastereoselectivity generally increases with increasing nucleophilicity of PR3 and decreases in the series 1β > 1α > 9. The highest diastereoselectivity was observed in the reaction of 1β with P(C6H4CH3-p)3. Predominantly, the isomer with the (S) configuration at the metal [(SMn)-2β] was formed which could be separated from the diastereomeric mixture by chromatography and be obtained in a pure form. Subsequent reaction of (SMn)-2β with BF3 afforded the carbyne-manganese complex (SMn)-[(η5-C5H5){P(C6H4CH3-p)3}(CO)Mn[TRIPLE BOND]CPh]BF4. Chemische Berichte ; 129 (1996), 4. - S. 385-390

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