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Highly efficient asymmetric synthesis of enantiopure dihydro-1,2-oxazines: dual-organocatalyst-promoted asymmetric cascade reaction. 2012

Hua Lin, and Yu Tan, and Xing-Wen Sun, and Guo-Qiang Lin
Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, PR China.

A one-pot dual-organocatalyst-promoted asymmetric α-aminoxylation/aza-Michael/aldol consendation cascade reaction is presented. The targeted optically active 1,2-oxazine derivatives are synthesized in moderate yields (up to 70%), excellent enantioselectivities (ee >99% in all cases), and excellent diastereoselectivities (dr up to >99:1) under mild conditions. To further elucidate the synthetic utility of the cascade products, cleavage of the N-O bond is demonstrated and an enantiopure syn-1,4-amino alcohol derivative is achieved in excellent yield.

UI MeSH Term Description Entries
D010078 Oxazines Six-membered heterocycles containing an oxygen and a nitrogen.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D000605 Amino Alcohols Compounds possessing both a hydroxyl (-OH) and an amino group (-NH2). Alcohols, Amino
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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