Chiral Lewis Acid Promoted Asymmetric Michael Addition Reaction of 2-(Trimethylsilyloxy)furans

Hiroshi Kitajima; Tsutomu Katsuki

doi:10.1055/s-1997-3235

Synlett 1997; 1997(5): 568-570
DOI: 10.1055/s-1997-3235

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Chiral Lewis Acid Promoted Asymmetric Michael Addition Reaction of 2-(Trimethylsilyloxy)furans

Hiroshi Kitajima, Tsutomu Katsuki^*

^*Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812-81, Japan, Fax +81 92 642 2607

Abstract

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Lewis acid promoted Michael addition of 2-(trimethylsilyloxy)furan to 3-[(E)-2-butenoyl]-1,3-oxazolidin-2-one (2) was examined. A 1:1 complex prepared from scandium triflate and 3,3'-bis(diethylaminomethyl)-1,1'-bi-2-naphthol 5b in situ showed excellent anti-selectivity and moderate enantioselectivity, while Cu(II)-bis(oxazolines) complex exhibited excellent enantioselectivity and moderate to good anti-selectivity.

asymmetric Michael addition - scandium(III) triflate - binaphthol derivative - bis(oxazolines)

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