Highly diastereoselective alkylation of chiral Tin (II) enolates onto cyclic acyl imines. An efficient asymmetric synthesis of bicyclic alkaloids bearing a nitrogen atom ring …

…, M Ochiai, S Tsukagoshi, E Fujita

Index: Nagao; Dai; Ochiai; Tsukagoshi; Fujita Journal of Organic Chemistry, 1990 , vol. 55, # 4 p. 1148 - 1156

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Citation Number: 68

Abstract

" Method A prepared by reaction of 4 (S)-or 4 (R)-IPTT sodium salt with the corresponding acyl chloride in THF at room temperature. Method B: prepared by dehydrative condensation between 4 (S)-IPTT and the carboxylic acid in the presence of DCC-DMAP in CHzClz at room temperature.* Yellow oil. Yellow prisms, mp 80.5-81.5 OC (recrystallized from E40- hexane).[aInD is measured in degrees." Recorded at 25" C./Recorded at 23 OC. ...