Regiodivergent Intermolecular [3+2] Cycloadditions of Vinyl Aziridines and Allenes: Stereospecific Synthesis of Chiral Pyrrolidines

被引：58

作者：

Lin, Tao-Yan ^{[1
]}

Zhu, Chao-Ze ^{[1
]}

Zhang, Peichao ^{[1
]}

Wang, Yidong ^{[1
]}

Wu, Hai-Hong ^{[1
]}

Feng, Jian-Jun ^{[1
]}

Zhang, Junliang ^{[1
,2
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 36期

关键词：

cycloaddition; allenes; chirality; heterocycles; rhodium; INTRAMOLECULAR HYDROAMINATION; RING EXPANSIONS; ASYMMETRIC-SYNTHESIS; DIVERGENT SYNTHESIS; DIAZO-COMPOUNDS; ACID; HETEROCYCLES; ALLENAMIDES; ISOCYANATES; REARRANGEMENT;

D O I：

10.1002/anie.201605530

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first rhodium-catalyzed intermolecular [3+2] cycloaddition reaction of vinyl aziridines and allenes for the synthesis of enantioenriched functionalized pyrrolidines was realized. [3+2] cycloaddition with the proximal C=C bond of N-allenamides gave 3-methylene-pyrrolidines in high regio- and diastereoselectivity, whereas, 2-methylene-pyrrolidines were obtained as the major products by the cycloadditions of vinyl aziridines with the distal C=C bond of allenes. Use of readily available starting materials, a broad substrate scope, high selectivity, mild reaction conditions, as well as versatile functionalization of the cycloadducts make this approach very practical and attractive.

引用

页码：10844 / 10848

页数：5

共 50 条

[31] Efficient intermolecular 3+2 trapping of the Nazarov intermediate with vinyl sulfides
Mahmoud, Bahja
West, F. G.
[J]. TETRAHEDRON LETTERS, 2007, 48 (29) : 5091 - 5094
[32] Regioselectivity of [3+2] Cycloadditions of Heteroaryl Azides and Ethyl-Vinyl Ether
D'Auria, Maurizio
Racioppi, Rocco
Viggiani, Licia
[J]. CHEMISTRYSELECT, 2022, 7 (17):
[33] Intermolecular Electrophilic Addition of Epoxides to Alkenes: [3+2] Cycloadditions Catalyzed by Lewis Acids
Shuler, William G.
Combee, Logan A.
Falk, Isaac D.
Hilinski, Michael K.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3335 - 3338
[34] Perspectives on Intermolecular Azomethine Ylide [3+2] Cycloadditions with Non-Electrophilic Olefins
Otero-Fraga, Jorge
Montesinos-Magraner, Marc
Mendoza, Abraham
[J]. SYNTHESIS-STUTTGART, 2017, 49 (04): : 802 - 809
[35] Enantio- and Diastereoselective Synthesis of Chiral Allenes by Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reactions
Trost, Barry M.
Zell, Daniel
Hohn, Christoph
Mata, Guillaume
Maruniak, Autumn
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) : 12916 - 12920
[36] Ligand-controlled regiodivergent -allyl palladium catalysis enables a switch between [3+2] and [3+3] cycloadditions
Xia, Yu
Bao, Qiao-Fei
Li, Yuke
Wang, Li-Jing
Zhang, Bo-Sheng
Liu, Hong-Chao
Liang, Yong-Min
[J]. CHEMICAL COMMUNICATIONS, 2019, 55 (32) : 4675 - 4678
[37] Double [3+2] cycloadditions for diastereoselective synthesis of spirooxindole pyrrolizidines
Zhang, Xiaofeng
Ma, Xiaoming
Qiu, Weiqi
Awad, JohnMark
Zhang, Wei
[J]. GREEN PROCESSING AND SYNTHESIS, 2022, 11 (01) : 1128 - 1135
[38] 1,3-Carbon D-A strategy for [3+2] cycloadditions/annulations with imines: synthesis of functionalized pyrrolidines and related alkaloids
Kumar, Indresh
[J]. RSC ADVANCES, 2014, 4 (32) : 16397 - 16408
[39] [3+2] CYCLOADDITIONS OF ALLYLSILANES .5. SYNTHESIS OF BICYCLO[3.3.0]OCTANES BY DOMINO [3+2] CYCLOADDITIONS OF ALLYLSILANES AND 3-BUTYN-2-ONE
KNOLKER, HJ
GRAF, R
[J]. SYNLETT, 1994, (02) : 131 - 133
[40] Synthesis of substituted imidazolines via [3+2]-cycloaddition of aziridines with nitriles
Prasad, BAB
Pandey, G
Singh, VK
[J]. TETRAHEDRON LETTERS, 2004, 45 (06) : 1137 - 1141

← 1 2 3 4 5 →