The regioselective and stereospecific substitution of unsymmetrical 1, 2-diols using the 1, 3, 2λ 5-dioxaphospholane methodology.

A Pautard-Cooper, SA Evans, WR Kenan

Index: Pautard-Cooper, Anne; Evans Jr., Slayton A.; Kenan Jr., William Rand Tetrahedron, 1991 , vol. 47, # 9 p. 1603 - 1610

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Citation Number: 12

Abstract

Stercospecific tosylate (− OTs) or azide (N3−) substitution at the C-4 stereocenter of a monosubstituted 1, 3, 2λ5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1, 2-diol) is readily achieved by treatment with either p-toluenesulfonic acid (p-TsOH) in tetrahydrofuran solvent or p-TsOH/sodium azide in acetonitrile solvent, respectively.