40179-50-8Relevant articles and documents
Enantioselective syntheses of 2-alkyl-, 2,6-dialkylpiperidines and indolizidine alkaloids through diastereoselective Mannich-Michael reactions
Weymann, Markus,Pfrengle, Waldemar,Schollmeyer, Dieter,Kunz, Horst
, p. 1151 - 1160 (1997)
Aldimines of 2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamine react with 1-methoxy-3-trimethylsilyloxybuta-1,3-diene in a Mannich-Michael condensation reaction sequence to give 2-substituted N-galactosyl-5,6-dehydropiperidin-4-ones 3 with high diastereoselectivity. The X-ray analysis of the 2-propyl derivative 3a proved (R)-configuration of the major diastereomer and led to the correction of our earlier assignment of configuration for (-)-coniine hydrochloride 9a obtained from this intermediate. Despite their low reactivity, these enaminones 3 can be converted into chiral 2,6-cis-disubstituted piperidinones 12 with high stereoselectivity by reaction with organocuprates in combination with hard electrophiles. Enantiomerically pure alkaloids such as (-)-dihydropinidine and gephyrotoxine 167B have been synthesized according to this methodology.
4-[(4'-Methylphenyl)sulfonyl]-1-(trophenylphosphoranylidene)-2-butanone as a New Four-Carbon Synthon for Substituted Divinyl Ketones
Barco, Achille,Benetti, Simonetta,Risi, Carmela De,Marchetti, Paolo,Pollini, Gian Piero,Zanirato, Vinicio
, p. 975 - 986 (2007/10/03)
The title compound and the corresponding anion have been conveniently used as precursors of substituted divinylketones in both carbo- and heterocyclization reactions in one-pot, three-step sequences leading to a wide variety of substituted carbo- and heterocyclic ring systems, as well as to multifunctionalized linear carbon frameworks. The compounds generated through the use of this multi-coupling reagent represent useful synthons for the construction of natural compounds including (+/-)-epibatidine, (-)-anabasine and (+/-)-pyrenophorin.