Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4+2]-Annulation Reaction

被引：44

作者：

Danda, Adithi ^{[1
,2
]}

Kesava-Reddy, Naredla ^{[1
]}

Golz, Christopher ^{[2
]}

Strohmann, Carsten ^{[2
]}

Kumar, Kamal ^{[1
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, Otto Hahn Str 11, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fak Chem & Chem Biol, Otto Hahn Str 6, D-44221 Dortmund, Germany

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 11期

关键词：

DIELS-ALDER REACTION; 1,3-BIS-SILYL ENOL ETHERS; N-ACYL AMINOPHOSPHINES; 4+2 ANNULATION; NATURAL-PRODUCTS; DOMINO REACTIONS; DRUG DISCOVERY; ALLENOATES; CHROMONE; CYCLOADDITIONS;

D O I：

10.1021/acs.orglett.6b01030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic addition of the amino acid derived bifunctional N-acylaminophosphine to an alpha-substituted allene ester generated a zwitterionic dipole that engaged the vinylogous ester function of 3-cyano-chromones in a [4 + 2] annulation reaction to deliver tetrahydroxanthones embodying three consecutive chiral centers in high yields and with excellent enantioselectivities. The established asymmetric synthesis Anther paves the way to two different classes of complex, sp(3)-rich tetracyclic benzopyrans via efficient cascade reactions.

引用

页码：2632 / 2635

页数：4

共 50 条

[21] Phosphine-Catalyzed (4+2) Cycloaddition of Conjugated Dienes with Enones and Its Asymmetric Variant
Li, Ke
Gan, Zhenjie
Li, Er-Qing
Duan, Zheng
ORGANIC LETTERS, 2021, 23 (08) : 3094 - 3099
[22] Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation
Han, Xiaoyu
Yao, Weijun
Wang, Tianli
Tan, Yong Ren
Yan, Ziyu
Kwiatkowski, Jacek
Lu, Yixin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5643 - 5647
[23] Phosphine-Catalyzed Asymmetric Cycloaddition Reaction of Diazenes: Enantioselective Synthesis of Chiral Dihydropyrazoles
Wang, Chang
Chen, Yuehua
Li, Jingyu
Zhou, Leijie
Wang, Bo
Xiao, Yumei
Guo, Hongchao
ORGANIC LETTERS, 2019, 21 (18) : 7519 - 7523
[24] An application of the phosphine-catalyzed [4+2] annulation in indole alkaloid synthesis:: Formal syntheses of (±)-alstonerine and (±)-macroline
Tran, YS
Kwon, O
ORGANIC LETTERS, 2005, 7 (19) : 4289 - 4291
[25] Phosphine-Catalyzed (4+2) Annulation of Allenoates Bearing Acidic Hydrogen with 1,1-Dicyanoalkenes
Gao, Zhenzhen
Zhou, Xiaoming
Xie, Lei
Wang, Xuekun
Wang, Shiben
Liu, Honglei
Guo, Hongchao
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7169 - 7174
[26] Phosphine-Catalyzed Asymmetric Formal [4+2] Tandem Cyclization of Activated Dienes with Isatylidenemalononitriles: Enantioselective Synthesis of Multistereogenic Spirocyclic Oxindoles
Hu, Fang-Le
Wei, Yin
Shi, Min
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) : 736 - 742
[27] Phosphine-catalyzed [3+2] and [4+2] annulation reactions of ynones with barbiturate-derived alkenes
Gao, Xing
Li, Zhen
Yang, Wenjun
Liu, Yang
Chen, Wufeng
Zhang, Cheng
Zheng, Lufei
Guo, Hongchao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (25) : 5298 - 5307
[28] Diastereoselective Synthesis of 6-Trifluoromethyl-5,6-dihydropyrans via Phosphine-Catalyzed [4+2] Annulation of α-Benzylallenoates with Ketones
Wang, Tong
Ye, Song
ORGANIC LETTERS, 2010, 12 (18) : 4168 - 4171
[29] Phosphine-Catalyzed [4+2] Annulation of Allenoate with Sulfamate-Derived Cyclic 'mines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate
Mao, Biming
Shi, Wangyu
Liao, Jianning
Liu, Honglei
Zhang, Cheng
Guo, Hongchao
ORGANIC LETTERS, 2017, 19 (23) : 6340 - 6343
[30] Phosphine-Catalyzed Enantioselective [4+2] Cycloaddition-Semipinacol-Type-Rearrangement Reaction of Morita-Baylis-Hillman Carbonates
Zhong, Yuan
Zhao, Xiaoyun
Gan, Lu
Hong, Sihua
Jiang, Xianxing
ORGANIC LETTERS, 2018, 20 (14) : 4250 - 4254

← 1 2 3 4 5 →