Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins

被引：31

作者：

Sarkar, Rahul ^{[1
]}

Mitra, Sankash ^{[1
]}

Mukherjee, Santanu ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

CHEMICAL SCIENCE | 2018年 / 9卷 / 26期

关键词：

ASYMMETRIC UMPOLUNG ALLYLATION; SUBSTITUTION-REACTIONS; DECONJUGATED BUTENOLIDES; MICHAEL ADDITION; DEAROMATIZATION REACTION; VICINAL STEREOCENTERS; SYNERGISTIC IRIDIUM; CONJUGATE ADDITION; ACID DERIVATIVES; GAMMA-ALLYLATION;

D O I：

10.1039/c8sc02041h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first iridium-catalyzed enantioselective vinylogous allylic alkylation of coumarins is presented. Using easily accessible linear allylic carbonates as the allylic electrophile, this reaction installs unfunctionalized allyl groups at the -position of 4-methylcoumarins in an exclusively branched-selective manner generally in high yields with an excellent level of enantioselectivity (up to 99:1 er).

引用

页码：5767 / 5772

页数：6

共 50 条

[1] Iridium-catalyzed direct asymmetric vinylogous allylic alkylation
Shi, Chang-Yun
Xiao, Jun-Zhao
Yin, Liang
CHEMICAL COMMUNICATIONS, 2018, 54 (84) : 11957 - 11960
[2] Iridium-Catalyzed Enantioselective Formal α-Allylic Alkylation of Acrylonitrile
Roy, Pankaj
Mukherjee, Santanu
ORGANIC LETTERS, 2023, 25 (24) : 4520 - 4524
[3] Catalytic Enantioselective Vinylogous Allylic Alkylation of Coumarins
Kayal, Satavisha
Mukherjee, Santanu
ORGANIC LETTERS, 2017, 19 (18) : 4944 - 4947
[4] Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides
Hamilton, James Y.
Sarlah, David
Carreira, Erick M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7644 - 7647
[5] Direct, Enantioselective Iridium-Catalyzed Allylic Amination of Racemic Allylic Alcohols
Lafrance, Marc
Roggen, Markus
Carreira, Erick M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (14) : 3470 - 3473
[6] Iridium-Catalyzed Enantioselective Allylic Substitution
Takeuchi, Ryo
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (09) : 885 - 902
[7] Enantioselective Iridium-Catalyzed Allylic Cyclizations
Schafroth, Michael A.
Rummelt, Stephan M.
Sarlah, David
Carreira, Erick M.
ORGANIC LETTERS, 2017, 19 (12) : 3235 - 3238
[8] Iridium-catalyzed enantioselective allylic vinylation
Carreira, E.M. (carreira@org.chem.ethz.ch), 1600, American Chemical Society (135):
[9] Iridium-Catalyzed Enantioselective Allylic Alkynylation
Hamilton, James Y.
Sarlah, David
Carreira, Erick M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7532 - 7535
[10] Enantioselective Iridium-Catalyzed Allylic Arylation
Polet, Damien
Rathgeb, Xavier
Falciola, Caroline A.
Langlois, Jean-Baptiste
El Hajjaji, Samir
Alexakis, Alexandre
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) : 1205 - 1216

← 1 2 3 4 5 →