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Regio- and stereocontrolled catalytic palladium- and nickel 'ene-type' cyclizations

Published inPure and Applied Chemistry, vol. 62, no. 10, p. 1941-1948
Publication date1990
Abstract

Intramolecular Pd(0)- and Ni(0) catalyzed alkene allylations, coupled with ,&eliminations or methoxycarbonylations efficiently provide various carbo- and heterocycles in one synthetic operation. Particularly, the nickel(0) catalyzed reaction of acyclic allylic substrates proceeds in a clean 'em'-manner with excellent topological control of pre-existing over developing stereogenic centers. Cyclic allyl precursors undergo exclusive 'endo'-cyclizations permitting simple and selective cis- or trans-annulation processes via an almost 100% stereospecific C- 0 → C-Pd or C-Ni → C-C chirality transfer. Analogous chirality transfer was also observed starting from enantiomerically pure (E)- and (Z)- 4-acetoxy-6-aza-2,8-nonadienes.

Citation (ISO format)
VON OPPOLZER, Wolfgang. Regio- and stereocontrolled catalytic palladium- and nickel “ene-type” cyclizations. In: Pure and Applied Chemistry, 1990, vol. 62, n° 10, p. 1941–1948. doi: 10.1351/pac199062101941
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ISSN of the journal0033-4545
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