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DOI: 10.1055/s-2006-958447
Silver-Sensitive Enantioselectivity in Asymmetric Heck Reactions
Publication History
Publication Date:
20 December 2006 (online)
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Abstract
Amine- and pure Ag(I)-promoted asymmetric Heck cyclisations of 2-iodobut-2-enanilide 1 both gave the oxindole product (R)-(+)-2 in relatively low ee but the partial reduction of the silver salt promoted a substantially more stereocontrolled route to (S)-(-)-2 in a reaction in which the use of Strem Ag3PO4 gave the R-product and Aldrich Ag3PO4 gave the S-product.
Key words
palladium - silver - Heck reaction - asymmetric catalysis - ring closure
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References and Notes
McDermott, M. C. PhD Thesis, University of East Anglia, UK, 2005, submitted.
21McDermott, M. C.; Stephenson, G. R.; Walkington, A. J. in preparation.
23Samples taken by the SK233 were analysed using an Agilent 1100 series system equipped with a 50 mm × 2 mm Phenomenex Luna 3µ C18 (2) column and run at 220 nm using a H2O to H2O-MeCN (1:19) eluent, with the ratio of substrate to product peaks calibrated using an equimolar solution.
24Results obtained from chiral analysis using a Chiracel OJ column eluted with hexane-EtOH 99.5:0.5 were calibrated by comparison to chiral shift experiments for a series of references samples. The ee are generally reproducible within a ±2% error range.
25Relative nominal purities: Strem Ag3PO4 (99+%); Aldrich Ag3PO4 (98%).