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

页码：4103 / 4110

页数：8

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