Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, PR China.
Org Lett. 2012 Aug 3;14(15):3818-21. doi: 10.1021/ol301218x. Epub 2012 Jul 18.
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.
本文报道了一种一锅双有机催化剂促进的不对称α-氨氧化/氮杂-Michael/aldol 缩合级联反应。在温和条件下，以中等至良好的收率（最高达 70%）、优异的对映选择性（所有情况下 ee >99%）和优秀的非对映选择性（dr 最高达 >99:1）合成了目标手性 1,2-噁嗪衍生物。为了进一步阐明级联产物的合成实用性，证明了 N-O 键的断裂，并以优异的产率得到了对映纯的 syn-1,4-氨基醇衍生物。
