Enantioselective protonation of samarium enolates by a C 2-symmetric chiral diol

S Takeuchi, A Ohira, N Miyoshi, H Mashio…

Index: Takeuchi, Seiji; Ohira, Akiko; Miyoshi, Norikazu; Mashio, Hajime; Ohgo, Yoshiaki Tetrahedron: Asymmetry, 1994 , vol. 5, # 9 p. 1763 - 1780

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Citation Number: 32

Abstract

Abstract High enantioselectivity (up to 97% ee) have been achieved in the protonation of samarium enolates which were generated by SmI 2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C 2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.