Tetrahedron: Asymmetry

Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary

M Serizawa, S Fujinami, Y Ukaji, K Inomata

Index: Serizawa, Masakazu; Fujinami, Shuhei; Ukaji, Yutaka; Inomata, Katsuhiko Tetrahedron Asymmetry, 2008 , vol. 19, # 8 p. 921 - 931

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Citation Number: 13

Abstract

The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1- alkynes, to α-dinitrones derived from glyoxal and N-(4-isopropylbenzyl) hydroxylamine was investigated by utilizing dicyclohexyl (R, R)-tartrate as a chiral auxiliary. The addition reaction of methyl (2-phenylethynyl) zinc afforded the corresponding optically active C2- symmetric (R, R)-bis (hydroxylamine) derivative with enantioselectivities of 90% and 81% ...