Canadian Journal of Chemistry

… asymmetric allylic alkylation/carbonyl allylation reaction sequence-Applications to the syntheses of (+)-(3 R, 5 R)-3-hydroxy-5-decanolide and (-)-massoialactone

L Carosi, DG Hall

Index: Carosi, Lisa; Hall, Dennis G. Canadian Journal of Chemistry, 2009 , vol. 87, # 5 p. 650 - 661

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Citation Number: 13

Abstract

The use of different organomagnesium reagents in the copper-catalyzed allylic alkylation of 3-chloropropenyl boronates with chiral phosphoramidite ligands produces the desired α- substituted allylic boronate reagents in high regioselectivity and with modest to high enantioselectivities (up to 96% ee). The size of the incoming alkyl substituent from the organomagnesium reagent was found to impact the yield and selectivity of the allylic ...

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