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. 2003 Jun 12;5(12):2111-4.
doi: 10.1021/ol034525i.

Highly stereoselective anti SN2' substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents

Nicole Harrington-Frost  1 , Helena Leuser, M Isabel Calaza, Florian F Kneisel, Paul Knochel
Affiliations

Highly stereoselective anti SN2' substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents

Nicole Harrington-Frost et al. Org Lett. .

Abstract

[reaction: see text] Allylic substitution reactions of zinc-copper organometallics on (Z)-allylic pentafluorobenzoates proceed with very high regioselectivity and excellent anti selectivity. The high fidelity in transfer of stereochemical information allowed a short synthesis of (+)-ibuprofen (97% ee).

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