Enantioselective Conjugate Addition of Both Aromatic Ketones and Acetone to Nitroolefins Catalyzed by Chiral Primary Amines Bearing Multiple Hydrogen-Bonding Donors

被引：26
作者：
Sun, Zhong-Wen [1 ]
Peng, Fang-Zhi [1 ]
Li, Ze-Qian [1 ]
Zou, Li-Wei [1 ]
Zhang, Shao-Xiong [1 ]
Li, Xiang [1 ]
Shao, Zhi-Hui [1 ,2 ]
机构：
[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 08期
关键词：
ASYMMETRIC MICHAEL ADDITION; BIFUNCTIONAL ORGANOCATALYSTS; STEREOCONTROLLED CREATION; TERTIARY STEREOCENTERS; ADJACENT QUATERNARY; NITROALKENES; THIOUREAS; ALDEHYDES; NITROSTYRENES; ELEMENTS;
D O I：
10.1021/jo300011x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new class of chiral primary amine catalysts bearing multiple hydrogen-bonding donors have been designed and synthesized. The newly developed bifunctional organocatalysts efficiently catalyzed not only enantioselective conjugate addition of aromatic ketones to nitroolefins in good yields (up to 87%) with excellent enantioselectivities (97 -> 99% cc) but also enantioselective conjugate addition of acetone to nitroolefins in excellent yields (90-96%) with high enantioselectivities (up to 97% ee).
引用
收藏
页码：4103 / 4110
页数：8
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