Asymmetric Synthesis of Trisubstituted Allenes: Copper-Catalyzed Alkylation and Arylation of Propargylic Phosphates

被引：90

作者：

Uehling, Mycah R. ^{[1
]}

Marionni, Samuel T. ^{[1
]}

Lalic, Gojko ^{[1
]}

机构：

[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

AXIALLY CHIRAL ALLENYLSILANES; ARYLBORONIC ACIDS; STEREOSPECIFIC SYNTHESIS; ENANTIOENRICHED ALLENES; GOLDEN OPPORTUNITIES; COUPLING REACTION; ALCOHOLS; ESTERS; CARBOXYLATION; REARRANGEMENT;

D O I：

10.1021/ol2031119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of trisubstituted allenes is accomplished by copper-catalyzed alkylation and arylation of propargylic phosphates using organoboron nucleophiles. Excellent chirality transfer and regioselectivity, together with good functional group compatibility, were observed in reactions with both alkyl boranes and arylboronic esters.

引用

页码：362 / 365

页数：4

共 50 条

[1] Copper-Catalyzed Propargylic Substitution of Dichloro Substrates: Enantioselective Synthesis of Trisubstituted Allenes and Formation of Propargylic Quaternary Stereogenic Centers
Li, Hailing
Grassi, David
Guenee, Laure
Buergi, Thomas
Alexakis, Alexandre
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (50) : 16694 - 16706
[2] Asymmetric Semipinacol Rearrangement Enabled by Copper-Catalyzed Propargylic Alkylation
Gong, Fan
Meng, Xiangjian
Lan, Shouang
Liu, Jinggong
Yang, Shuang
Fang, Xinqiang
[J]. ACS CATALYSIS, 2022, 12 (19) : 12036 - 12044
[3] Synthesis of Conjugated Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Aryl- or Alkenylboronates
Yang, Mingyu
Yokokawa, Natsumi
Ohmiya, Hirohisa
Sawamura, Masaya
[J]. ORGANIC LETTERS, 2012, 14 (03) : 816 - 819
[4] Copper-catalyzed asymmetric propargylic substitution of anthrones and propargylic esters
Zhiheng Li
Danran Li
Huaming Xiang
Jian Huang
Yinuo Zheng
Cuiju Zhu
Xiuling Cui
Chao Pi
Hao Xu
[J]. Chinese Chemical Letters, 2022, (02) : 867 - 870
[5] General Approach to Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes
Ohmiya, Hirohisa
Yokobori, Umi
Makida, Yusuke
Sawamura, Masaya
[J]. ORGANIC LETTERS, 2011, 13 (23) : 6312 - 6315
[6] Copper-catalyzed asymmetric propargylic substitution of anthrones and propargylic esters
Li, Zhiheng
Li, Danran
Xiang, Huaming
Huang, Jian
Zheng, Yinuo
Zhu, Cuiju
Cui, Xiuling
Pi, Chao
Xu, Hao
[J]. CHINESE CHEMICAL LETTERS, 2022, 33 (02) : 867 - 870
[7] Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols
Li, Hui
Li, Xiaoxun
Wang, Hao-Yuan
Winston-McPherson, Gabrielle N.
Geng, Hao-miao Julie
Guzei, Ilia A.
Tang, Weiping
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (82) : 12293 - 12296
[8] Copper-catalyzed asymmetric allylic alkylation
Falciola, Caroline A.
Alexakis, Alexandre
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (22) : 3765 - 3780
[9] Asymmetric synthesis of α-chiral β-hydroxy allenes: copper-catalyzed γ-selective borylative coupling of vinyl arenes and propargyl phosphates
Han, Jung Tae
Yun, Jaesook
[J]. CHEMICAL COMMUNICATIONS, 2019, 55 (66) : 9813 - 9816
[10] Photoredox/nickel dual-catalyzed regioselective alkylation of propargylic carbonates for trisubstituted allenes
Zhou, Zhao-Zhao
Song, Xian-Rong
Du, Sha
Xia, Ke-Jian
Tian, Wan-Fa
Xiao, Qiang
Liang, Yong-Min
[J]. CHEMICAL COMMUNICATIONS, 2021, 57 (74) : 9390 - 9393

← 1 2 3 4 5 →