Diastereo- and enantioselective aldol reaction of granatanone (pseudopelletierine) |
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| Authors: | Ryszard Lazny Karol WolosewiczPaulina Zielinska Zofia Urbanczyk-LipkowskaPrzemyslaw Kalicki |
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| Affiliation: | a Institute of Chemistry, University of Bialystok, ul. Hurtowa 1, 15-339 Bialystok, Poland
b Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw 48, Poland |
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| Abstract: | Granatanone (granatan-3-one, 9-methyl-9-azabicyclo[3.3.1]nonan-3-one, pseudopelletierine or pseudopelletrierin) undergoes deprotonation with lithium amides giving a lithium enolate, which reacts with aldehydes diastereoselectively giving exclusively exo isomers and anti/syn selectivity up to 98:2. Granatanone can be enantioselectively lithiated by chiral lithium amides and the resulting non-racemic enolate can be reacted with aldehydes giving aldols with enantiomeric excess up to 93% (99% ee after recrystallization). The absolute and relative configuration of the aldol products was determined by NMR spectroscopy and X-ray analysis.Granatanone; aldol reaction; asymmetric synthesis; enantioselective deprotonation; chiral lithium amide. |
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| Keywords: | Chiral lithium amide Aldol reaction Granatanone Stereoselective synthesis Enantioselective synthesis |
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