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

被引：31
作者：
Lin, Hue [1 ]
Tan, Yu [1 ]
Sun, Xing-Wen [1 ]
Lin, Guo-Qiang [1 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 15期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTION; NITROSO ALDOL/MICHAEL REACTION; ENANTIOSELECTIVE SYNTHESIS; ALPHA-AMINOXYLATION; DIASTEREOSELECTIVE SYNTHESIS; ORGANOCASCADE CATALYSIS; ORGANIC CATALYSIS; ENAMINE CATALYSIS; DOMINO REACTIONS; STEREOCENTERS;
D O I：
10.1021/ol301218x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：3818 / 3821
页数：4
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