Synthesis of Isoquinuclidines via Dearomative Diels-Alder Reaction of Cyclic Amidines with Indoles

被引：1

作者：

You, Xiaobin ^{[1
]}

Yao, Ying ^{[1
]}

Liu, Pengyutian ^{[2
]}

Chen, Lu ^{[2
]}

Xie, Yubao ^{[2
]}

Li, Guofeng ^{[2
]}

Hong, Liang ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China

[2] Shenzhen Univ, Sch Pharm, Med Sch, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 05期

关键词：

BISINDOLE ALKALOIDS; CYCLOADDITION; 1,2-DIHYDROPYRIDINES; CONSTRUCTION; IBOGAN;

D O I：

10.1021/acs.joc.3c02736

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development and utilization of new dienes and dienophiles for the controlled synthesis of isoquinuclidines is highly appealing. Herein, we describe a novel strategy for diastereoselective synthesis of indoline-fused isoquinuclidines via copper-catalyzed dearomative Diels-Alder reaction of cyclic amidines with indoles. This protocol avoids the use of unstable DHPs and activated alkenes, offering a more efficient and selective approach to synthesize isoquinuclidines.

引用

页码：3635 / 3643

页数：9

共 50 条

[1] Synthesis of Isoquinuclidines from Highly Substituted Dihydropyridines via the Diels-Alder Reaction
Martin, Rhia M.
Bergman, Robert G.
Ellman, Jonathan A.
ORGANIC LETTERS, 2013, 15 (03) : 444 - 447
[2] An efficient synthesis of chiral isoquinuclidines by Diels-Alder reaction using Lewis acid catalyst
Hirama, Masafumi
Kato, Yuji
Seki, Chigusa
Nakano, Hiroto
Takeshita, Mitsuhiro
Oshikiri, Noriko
Iyoda, Masahiko
Matsuyama, Haruo
TETRAHEDRON, 2010, 66 (38) : 7618 - 7624
[3] SYNTHESIS OF NEW POLYMERS VIA DIELS-ALDER REACTION
KUHRAU, M
STADLER, R
MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1990, 11 (12): : 635 - 644
[4] Synthesis of cyclodextrin dimers via Diels-Alder reaction
Miyagawa, Atsushi
Hasegawa, Takuya
Yamamura, Hatsuo
SYNTHETIC COMMUNICATIONS, 2023, 53 (22) : 1878 - 1885
[5] ALKALOID SYNTHESIS VIA THE IMINO DIELS-ALDER REACTION
WEINREB, SM
GOBAO, RA
BREMMER, M
BAILEY, TR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1982, 183 (MAR): : 105 - ORGN
[6] Synthesis of cyclic peroxides via enyne-RCM/Diels-Alder reaction sequence
Yang, YK
Lee, S
Tae, J
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (09) : 1307 - 1308
[7] DIELS-ALDER REACTIONS OF INDOLES
KRAUS, GA
RAGGON, J
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 30 - ORGN
[8] Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diels-Alder Reaction
Kamo, Shogo
Kurosawa, Hitomi
Matsuzawa, Akinobu
Sugita, Kazuyuki
ORGANIC LETTERS, 2022, 24 (03) : 921 - 923
[9] Total synthesis of (+)-cassaine via transannular diels-alder reaction
Phoenix, Serge
Reddy, Maddi Sridhar
Deslongchamps, Pierre
Journal of the American Chemical Society, 2008, 130 (42): : 13989 - 13995
[10] Enantioselective synthesis of cyclic ethers via hetero Diels-Alder reaction. Formal synthesis of (+)- and (-)-laurecin
Mujica, MT
Afonso, MM
Galindo, A
Palenzuela, JA
SYNLETT, 1996, (10) : 983 - &

← 1 2 3 4 5 →