Highly Efficient Asymmetric Synthesis of Enantiopure Dihydro-1,2-oxazines: Dual-Organocatalyst-Promoted Asymmetric Cascade Reaction

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 excellen...

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Bibliographic Details
Published in:Organic letters 2012-08, Vol.14 (15), p.3818-3821
Main Authors: Lin, Hua, Tan, Yu, Sun, Xing-Wen, Lin, Guo-Qiang
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Catalysis
Molecular Structure
Oxazines - chemical synthesis
Oxazines - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301218x