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Publication Type : Journal Article
Publisher : American Chemical Society
Source : Organic Letters, 2012
Campus : Amritapuri
School : School of Biotechnology
Verified : No
Year : 2012
Abstract : (S)-4-Isopropyl-1-phenyltetrahydropyrimidin-2(1H)-one was synthesized and evaluated as a chiral auxiliary for asymmetric acetate and propionate aldol reactions, by generation of titanium and lithium enolates, affording excellent yields and stereoselectivities for syn and anti aldol diastereomers, respectively. High stereoselectivities were also obtained in lithium mediated alkylation reactions. The application of the auxiliary was exemplified in the asymmetric synthesis of a natural oxyneolignan, (+)-(7S,8S)-4-hydroxy-3,3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneoligna-7,9-diol-7′-oic acid.
Cite this Research Publication : Mangilal Chouhan, Ratnesh Sharma and Vipin A. Nair, "Stereoregulations of pyrimidinone based chiral auxiliary in aldol and alkylation reactions: a convenient route to oxyneolignans" Organic Letters, 2012, 14, 5672-5675