Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates

被引:31
作者
Wang, Hui [1 ]
Xu, Ming-Hua [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 15期
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; cyclization; arylation; rhodium; boron; ligands; sulfamidates; heterocycles; OLEFIN LIGANDS; NUCLEOPHILIC DISPLACEMENTS; ALPHA-KETOESTERS; CHIRAL LIGANDS; FACILE ENTRY; SULFAMATE; AZIRIDINATION; 1,2-ADDITION; ALLOSAMINE; AMIDATION;
D O I
10.1055/s-0033-1338418
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient asymmetric arylation of cyclic N-sulfonyl aldimines with arylboronic acids catalyzed by a rhodium/sulfur-olefin ligand complex under mild conditions is described. A wide range 4-aryl-3,4-dihydro-1,2,3-benzoxathiazine 2,2-dioxides were obtained in extremely high yields (93-99%) and high enantiomeric purities (97-99% ee).
引用
收藏
页码:2125 / 2133
页数:9
相关论文
共 57 条
[41]  
Nicolaou KC, 2002, ANGEW CHEM INT EDIT, V41, P834, DOI 10.1002/1521-3773(20020301)41:5<834::AID-ANIE834>3.0.CO
[42]  
2-V
[43]   Asymmetric Synthesis of (Triaryl)methylamines by Rhodium-Catalyzed Addition of Arylboroxines to Cyclic N-Sulfonyl Ketimines [J].
Nishimura, Takahiro ;
Noishiki, Akira ;
Tsui, Gavin Chit ;
Hayashi, Tamio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5056-5059
[44]  
Petry S., 2002, WO, Patent No. 2002011722
[45]  
Posakony JJ, 2002, SYNTHESIS-STUTTGART, P766
[46]   Design of Chiral Sulfoxide-Olefins as a New Class of Sulfur-Based Olefin Ligands for Asymmetric Catalysis [J].
Qi, Wei-Yi ;
Zhu, Ting-Shun ;
Xu, Ming-Hua .
ORGANIC LETTERS, 2011, 13 (13) :3410-3413
[47]   Improved and efficient synthesis of chiral N,P-Ligands via cyclic sulfamidates for asymmetric addition of butyllithium to benzaldehyde [J].
Ronnholm, Petra ;
Sodergren, Mikael ;
Hilmersson, Goran .
ORGANIC LETTERS, 2007, 9 (19) :3781-3783
[48]   Sulfoxide-Alkene Hybrids: A New Class of Chiral Ligands for the Hayashi-Miyaura Reaction [J].
Thaler, Tobias ;
Guo, Li-Na ;
Steib, Andreas K. ;
Raducan, Mihai ;
Karaghiosoff, Konstantin ;
Mayer, Peter ;
Knochel, Paul .
ORGANIC LETTERS, 2011, 13 (12) :3182-3185
[49]   Simple Branched Sulfur-Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters [J].
Wang, Hui ;
Jiang, Tao ;
Xu, Ming-Hua .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (03) :971-974
[50]   Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters [J].
Wang, Hui ;
Zhu, Ting-Shun ;
Xu, Ming-Hua .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (46) :9158-9164