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Magnesiated Unsaturated Silylated Cyanohydrins as Synthetic Equivalents of Aromatic and Heterocyclic Grignard Reagents Bearing a Ketone or an Aldehyde

Ching-Yuan Liu, Hongjun Ren and Paul Knochel*

*Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 München, Germany, Email: paul.knochelcup.uni-muenchen.de

C.-Y. Liu, H. Ren, P. Knochel, Org. Lett., 2006, 8, 617-629.

DOI: 10.1021/ol052792d (free Supporting Information)


Abstract

Silylated cyanohydrins of iodo-substituted aryl, heteroaryl, or cycloalkenyl ketones undergo an I/Mg-exchange using i-PrMgCl·LiCl. After subsequent reactions with electrophiles, a facile deprotection produces polyfunctional ketones in good overall yiels. An extension to aromatic iodoaldehydes is described.

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Key Words

Grignard Reagents, Cyanohydrins, Aryl Ketones, Substituted Enones, Allylation, Deprotection (Aldehydes, Ketones)


ID: J54-Y2006-510