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

S Fukuzawa, I Oura, K Shimizu…

Index: Fukuzawa, Shin-Ichi; Oura, Ichiro; Shimizu, Kenta; Kato, Minoru; Ogata, Ken-Ichi European Journal of Organic Chemistry, 2009 , # 5 p. 716 - 720

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Citation Number: 6

Abstract

Abstract The pinacol coupling reaction of (Rp)-2-diphenylphosphanyl ferrocenecarbaldehyde (1) was smoothly mediated by divalent samarium triflate to give (R, R)-diol 2a predominantly, whereas the use of samarium (II) iodide resulted in low selectivity as described in the previous literature. In contrast, the coupling reaction of (Rp)-2- diphenylphosphoryl ferrocenecarbaldehyde (3) with Sm (OTf) 2 gave the (S, S)-diol as the ...