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

被引：107

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

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 19期

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

页码：5022 / 5025

页数：4

共 67 条

[21] Weak Bronsted Acid-Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet-Spengler Reactions
Klausen, Rebekka S.
Jacobsen, Eric N.
[J]. 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
Komanduri, Venukrishnan
Krische, Michael J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) : 16448 - 16449
[23] Thiourea-Catalyzed Enantioselective Iso-Pictet-Spengler Reactions
Lee, Yunmi
Klausen, Rebekka S.
Jacobsen, Eric N.
[J]. ORGANIC LETTERS, 2011, 13 (20) : 5564 - 5567
[24] Chiral Counteranion-Aided Asymmetric Hydrogenation of Acyclic Imines
Li, Chaoqun
Wang, Chao
Villa-Marcos, Barbara
Xiao, Jianliang
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) : 14450 - +
[25] Metal-Bronsted Acid Cooperative Catalysis for Asymmetric Reductive Amination
Li, Chaoqun
Villa-Marcos, Barbara
Xiao, Jianliang
[J]. 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
Liao, Xuebin
Zhou, Hao
Yu, Jianming
Cook, James M.
[J]. 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
Liu, Xin-Yuan
Che, Chi-Ming
[J]. ORGANIC LETTERS, 2009, 11 (18) : 4204 - 4207
[28] The Asymmetric Pictet-Spengler Reaction
Lorenz, Michael
Van Linn, Michael L.
Cook, James M.
[J]. 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
Ma, Jun
Yin, Wenyuan
Zhou, Hao
Cook, James M.
[J]. ORGANIC LETTERS, 2007, 9 (18) : 3491 - 3494
[30] Catalytic asymmetric total synthesis of (+)-yohimbine
Mergott, Dustin J.
Zuend, Stephan J.
Jacobsen, Eric N.
[J]. ORGANIC LETTERS, 2008, 10 (05) : 745 - 748

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