Enantioselective 1,6-Addition of β-Ketoester Enolates to In Situ Generated para-Quinone Methides Enabled by Cooperative Palladium and Bronsted Acid Catalysis

被引：6

作者：

Gaertner, Cornelius, V ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

[1] Univ Leipzig, Inst Organ Chem, D-04103 Leipzig, Germany

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 02期

关键词：

ASYMMETRIC ADDITION; 1,3-DICARBONYL COMPOUNDS; MICHAEL REACTION; FLUORINATION; COMPLEXES; IMINES;

D O I：

10.1021/acs.orglett.2c04127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an asymmetric cooperative process for the enantioselective 1,6-addition of fi-ketoesters to in situ generated para-quinone methides with chiral Pd-aqua complexes as mixed Bronsted acid-base catalysts. Excellent yields, outstanding enantiocontrol, and good diastereoselectivity across a broad substrate range are highlights of this transformation. The utility of this reaction is further demonstrated by a facile scale up and subsequent complexity-increasing modifications. '

引用

页码：416 / 420

页数：5

共 50 条

[31] Base-promoted 1,6-conjugate addition of alkylazaarenes to para-quinone methides
Rayaroth, Amritha
Singh, Rajat Kumar
Kalyanakrishnan, A., V
Hari, Krishna
Katiyamoorthy, Alagiri
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (17) : 3354 - 3359
[32] Scandium(III)-Catalysed Decarboxylative Addition of β-Ketoacids to para-Quinone Methides: Evidence for 1,6-Addition and Base-Assisted Decarboxylation Tandem Process
Jiang, Chunhui
Chen, Yayun
Huang, Gaokui
Ni, Cheng
Liu, Xiaoqian
Lu, Hongfei
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (02) : 257 - 260
[33] Enantioselective Rauhut-Currier-Type 1,6-Conjugate Addition of Methyl Vinyl Ketone to para-Quinone Methides
Kang, Tian-Chen
Wu, Lu-Ping
Yu, Qi-Wen
Wu, Xin-Yan
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (27) : 6509 - 6513
[34] Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides
Zhang, Xiang-Zhi
Deng, Yu-Hua
Yan, Xu
Yu, Ke-Yin
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13): : 5655 - 5662
[35] Stereoselective 1,6-Conjugate Addition/Annulation of para-Quinone Methides with Vinyl Epoxides/Cyclopropanes
Ma, Chao
Huang, Yuan
Zhao, Yu
ACS CATALYSIS, 2016, 6 (10): : 6408 - 6412
[36] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
Chu, Wen-Dao
Zhang, Le-Fen
Bao, Xu
Zhao, Xian-He
Zeng, Chao
Du, Ji-Yuan
Zhang, Guo-Biao
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
[37] Bronsted acid-catalyzed 1,6-hydrophosphination of propargylic para-quinone methides and aza-para-quinone methides for the rapid construction of phosphorus-substituted quaternary carbon centers
Xiong, Ting
Yuan, Hao
Yang, Fuxing
Jiang, Jun
GREEN SYNTHESIS AND CATALYSIS, 2022, 3 (01): : 46 - 52
[38] Synthesis of Functionalized Benzofurans from para-Quinone Methides via Phospha-1,6-Addition/O-Acylation/Wittig Pathway
Liou, Yan-Cheng
Karanam, Praneeth
Jang, Yeong-Jiunn
Lin, Wenwei
ORGANIC LETTERS, 2019, 21 (19) : 8008 - 8012
[39] Direct access to a,a′-diarylated ketones through N-heterocyclic carbene-catalyzed 1,6-addition of aromatic aldehydes to para-quinone methides
Zhang, Guifu
Jiang, Longxiang
Shi, Wenjuan
Zhou, Meiling
Qiu, Fenghao
Sun, Shaofa
Wang, Jian
Guo, Haibing
SYNTHETIC COMMUNICATIONS, 2017, 47 (08) : 803 - 810
[40] Tandem 1,6-addition/cyclopropanation/rearrangement reaction of vinylogous para-quinone methides with 3-chlorooxindoles: construction of vicinal quaternary carbon centers
Pan, Yuan
Ren, Weiwu
Zhang, Zhanhao
Luo, Fengbiao
Hou, Xiaohan
Li, Xiaoyang
Yang, Yun-Fang
Wang, Yang
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (14): : 3697 - 3708

← 1 2 3 4 5 →