Journal
ORGANIC LETTERS
Volume 14, Issue 15, Pages 3818-3821Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol301218x
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Funding
- National Natural Science Foundation of China [21072031, 20802009]
- Shanghai Municipal Committee of Science and Technology [10ZR1404100]
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A one-pot dual-organocatalyst-promoted asymmetric alpha-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.
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