Diastereo- and enantioselective aldol reaction of granatanone (pseudopelletierine)

Autor:	Zofia Urbańczyk-Lipkowska, Karol Wolosewicz, Przemysław Kalicki, Paulina Zielinska, Ryszard Lazny
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Lithium amide Organic Chemistry Enantioselective synthesis Biochemistry Aldehyde chemistry.chemical_compound Pseudopelletierine Deprotonation Aldol reaction chemistry Drug Discovery Organic chemistry Aldol condensation Enantiomeric excess
Zdroj:	Tetrahedron. 67:9433-9439
ISSN:	0040-4020
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::127b77de57842c56523a1ffa9e500bad https://doi.org/10.1016/j.tet.2011.09.096 Zobrazit plný text záznamu Full Text from ScienceDirect