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

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• 作者：Masakazu Serizawa ; Shuhei Fujinami ; Yutaka Ukaji ; Katsuhiko Inomata
• 关键词：Carbohydrate ; Protein ; Lactose ; Exercise
• 刊名：Tetrahedron: Asymmetry
• 出版年：2008
• 出版时间：1 May 2008
• 年：2008
• 卷：19
• 期：8
• 页码：921-931
• 全文大小：299 K

文摘

The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to -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 % ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities.