Palladium-Catalyzed Asymmetric Nitrogen-Selective Addition Reaction of Indoles to Alkoxyallenes

被引：36

作者：

Jang, Seok Hyeon ^{[1
]}

Kim, Hyun Woo ^{[2
]}

Jeong, Wook ^{[1
]}

Moon, Dohyun ^{[3
]}

Rhee, Young Ho ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol, Dept Chem, 77 Cheongam Ro, Pohang 37673, Gyeongbuk, South Korea

[2] Korea Res Inst Chem Technol, Ctr Mol Modeling & Simulat, 141 Gajeongro, Daejeon 34114, South Korea

[3] Pohang Accelerator Lab, Beamline Dept, 80 Jigokro 127 Beongil, Pohang 37673, Gyeongbuk, South Korea

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

DE-NOVO SYNTHESIS; ALLYLIC ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; N-ALLYLINDOLES; ALLYLATION; INDOLINES; ALLENES; CARBOXYLATION; CONSTRUCTION;

D O I：

10.1021/acs.orglett.8b00191

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new palladium-catalyzed asymmetric addition reaction of indoles to alkoxyallenes is reported. Remarkably, the reaction showed complete regioselectivity toward the nitrogen. A new mechanism distinct from that of conventional pi-allyl chemistry is proposed to explain this unique selectivity. The utility of the reaction is demonstrated by highly efficient and flexible synthesis of N-glycosylindoles.

引用

页码：1248 / 1251

页数：4

共 45 条

[11] Palladium-Catalyzed Intramolecular Arylative Carboxylation of Allenes with CO2 for the Construction of 3-Substituted Indole-2-carboxylic Acids [J].

Higuchi, Yuki ;

Mita, Tsuyoshi ;

Sato, Yoshihiro .

ORGANIC LETTERS, 2017, 19 (10) :2710-2713

[12] Palladium-catalyzed β-allylation of 2,3-disubstituted indoles [J].

Kagawa, Natsuko ;

Malerich, Jeremiah P. ;

Rawal, Viresh H. .

ORGANIC LETTERS, 2008, 10 (12) :2381-2384

[13] Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene [J].

Kang, Soyeong ;

Jang, Seok Hyeon ;

Lee, Juyeol ;

Kim, Dong-gil ;

Kim, Mijin ;

Jeong, Wook ;

Rhee, Young Ho .

ORGANIC LETTERS, 2017, 19 (17) :4684-4687

[14] The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C-C Bond Formation [J].

Keith, John A. ;

Behenna, Douglas C. ;

Sherden, Nathaniel ;

Mohr, Justin T. ;

Ma, Sandy ;

Marinescu, Smaranda C. ;

Nielsen, Robert J. ;

Oxgaard, Jonas ;

Stoltz, Brian M. ;

Goddard, William A., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (46) :19050-19060

[15] A Perspective on the Stereodefined N,O-Acetals: Synthesis and Potential Applications [J].

Kim, Haejin ;

Rhee, Young Ho .

SYNLETT, 2012, (20) :2875-2879

[16] Synthetic Strategy for Cyclic Amines: A Stereodefined Cyclic N,O-Acetal as a Stereocontrol and Diversity-Generating Element [J].

Kim, Haejin ;

Lim, Wontaeck ;

Im, Donghong ;

Kim, Dong-gil ;

Rhee, Young Ho .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12055-12058

[17] Stereodefined N,O-Acetals: Pd-Catalyzed Synthesis from Homopropargylic Amines and Utility in the Flexible Synthesis of 2,6-Substituted Piperidines [J].

Kim, Haejin ;

Rhee, Young Ho .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (09) :4011-4014

[18] De Novo Synthesis of Furanose Sugars: Catalytic Asymmetric Synthesis of Apiose and Apiose-Containing Oligosaccharides [J].

Kim, Mijin ;

Kang, Soyeong ;

Rhee, Young Ho .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) :9733-9737

[19]

Kinderman SS, 2002, ADV SYNTH CATAL, V344, P736, DOI 10.1002/1615-4169(200208)344:6/7<736::AID-ADSC736>3.0.CO

[20]

2-8

← 1 2 3 4 5 →