Tetrahedron

On the diastereoselectivity of cyanide addition to β-hydroxyketones: One-pot synthesis of syn β-hydroxycyanohydrins and anti 2, 4-dihydroxyamides

MS Batra, FJ Aguilar, E Brunet

文献索引：Batra, Manohar Singh; Aguilar, Francisco J.; Brunet, Ernesto Tetrahedron, 1994 , vol. 50, # 27 p. 8169 - 8184

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被引用次数: 6

摘要

The intrinsic stereoselectivity of the cyanide addition to β-hydroxyketones in the presence of 18-crown-6 or ZnI2 is lower than that previously reported. However, the reaction bears a practical value in that syn β-hydroxycyanohydrins and anti 2, 4-dihydroxyamides can be diastereoselectivity obtained in reasonable yields in a one-pot procedure. The high de's initially reported were due to the work-up procedure, where the HCl converted much faster ...