Divalent Samarium Triflate Mediated Stereoselective Pinacol Coupling of Planar Chiral Phosphanyl and Phosphoryl Ferrocenecarbaldehyde

Autor: Fukuzawa, Shinichi, Oura, Ichiro, Shimizu, Kenta, Kato, Minoru, Ogata, Kenichi
Zdroj: European Journal of Organic Chemistry; February 2009, Vol. 2009 Issue: 5 p716-720, 5p
Abstrakt: The pinacol coupling reaction of Rp2diphenylphosphanyl ferrocenecarbaldehyde 1 was smoothly mediated by divalent samarium triflate to give R,Rdiol 2apredominantly, whereas the use of samariumII iodide resulted in low selectivity as described in the previous literature. In contrast, the coupling reaction of Rp2diphenylphosphoryl ferrocenecarbaldehyde 3 with SmOTf2gave the S,Sdiol as the major isomer, which was the opposite stereochemistry of that obtained in the reaction with 1. The rhodium complexes of diphosphanes 2awere good catalysts for the asymmetric hydrogenation of αacetamidocinnamic acid, and the product was obtained quantitatively with up to 92  ee. © WileyVCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009
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