Addition of Grignard Reagents to α-Epoxy N-Sulfonyl Hydrazones

The development of a broadly applicable approach to the asymmetric α-alkylation of ketones is a long-standing and – until recently – unresolved problem in the field of organic synthesis. Recently, Professor Don M. Coltart and co-workers from the University of Houston (Texas, USA) reported the development of the broadest method ever reported for the α-functionalization of ketones or their derivatives. The article describes the highly (up to >25:1) syn-selective formation of β-hydroxy N-sulfonyl hydrazones having α-tertiary or α-quaternary centers by the simple combination of Grignard reagents – the most readily available and common of all organometallic reagents – and α-epoxy N-sulfonyl hydrazones.

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