Ring-Closing Metathesis/Isomerization/Pictet-Spengler Cascade via Ruthenium/Chiral Phosphoric Acid Sequential Catalysis

被引:108
作者
Cai, Quan [1 ]
Liang, Xiao-Wei [1 ]
Wang, Shou-Guo [1 ]
Zhang, Jun-Wei [1 ]
Zhang, Xiao [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE BRONSTED ACID; BIOMIMETIC ASYMMETRIC HYDROGENATION; NONREARRANGED MONOTERPENOID UNIT; ACYLIMINIUM CYCLIZATION CASCADES; SIMPLE INDOLE ALKALOIDS; PICTET-SPENGLER; RELAY CATALYSIS; BINARY-SYSTEM; COOPERATIVE CATALYSIS; 3-COMPONENT REACTIONS;
D O I
10.1021/ol302215u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral phosphoric acid worked together with Hoveyda-Grubbs II catalyst enabling highly efficient synthesis of enantioenriched tetrahydro-beta-carbolines (up to 98% yield, 99% ee) through a ring-closing metathesis/isomerization/Pictet-Spengler cascade reaction via sequential catalysis.
引用
收藏
页码:5022 / 5025
页数:4
相关论文
共 67 条
[21]   Weak Bronsted Acid-Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet-Spengler Reactions [J].
Klausen, Rebekka S. ;
Jacobsen, Eric N. .
ORGANIC LETTERS, 2009, 11 (04) :887-890
[22]   Enantioselective reductive coupling of 1,3-enynes to heterocyclic aromatic aldehydes and ketones via rhodium-catalyzed asymmetric hydrogenation: Mechanistic insight into the role of Bronsted acid additives [J].
Komanduri, Venukrishnan ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16448-16449
[23]   Thiourea-Catalyzed Enantioselective Iso-Pictet-Spengler Reactions [J].
Lee, Yunmi ;
Klausen, Rebekka S. ;
Jacobsen, Eric N. .
ORGANIC LETTERS, 2011, 13 (20) :5564-5567
[24]   Chiral Counteranion-Aided Asymmetric Hydrogenation of Acyclic Imines [J].
Li, Chaoqun ;
Wang, Chao ;
Villa-Marcos, Barbara ;
Xiao, Jianliang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14450-+
[25]   Metal-Bronsted Acid Cooperative Catalysis for Asymmetric Reductive Amination [J].
Li, Chaoqun ;
Villa-Marcos, Barbara ;
Xiao, Jianliang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6967-+
[26]   An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)-talcarpine and (-)-anhydromacrosalhine-methine [J].
Liao, Xuebin ;
Zhou, Hao ;
Yu, Jianming ;
Cook, James M. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8884-8890
[27]   Highly Enantioselective Synthesis of Chiral Secondary Amines by Gold(I)/Chiral Bronsted Acid Catalyzed Tandem Intermolecular Hydroamination and Transfer Hydrogenation Reactions [J].
Liu, Xin-Yuan ;
Che, Chi-Ming .
ORGANIC LETTERS, 2009, 11 (18) :4204-4207
[28]   The Asymmetric Pictet-Spengler Reaction [J].
Lorenz, Michael ;
Van Linn, Michael L. ;
Cook, James M. .
CURRENT ORGANIC SYNTHESIS, 2010, 7 (03) :189-223
[29]   Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-Methoxy-Nb-methylgeissoschizol [J].
Ma, Jun ;
Yin, Wenyuan ;
Zhou, Hao ;
Cook, James M. .
ORGANIC LETTERS, 2007, 9 (18) :3491-3494
[30]   Catalytic asymmetric total synthesis of (+)-yohimbine [J].
Mergott, Dustin J. ;
Zuend, Stephan J. ;
Jacobsen, Eric N. .
ORGANIC LETTERS, 2008, 10 (05) :745-748