Electronic tuning of chiral diene ligands in iridium-catalyzed asymmetric 1,6-addition of arylboroxines to δ-aryl-α,β,γ,δ-unsaturated ketones

被引：51

作者：

Nishimura, Takahiro ^{[1
]}

Noishiki, Akira ^{[1
]}

Hayashi, Tamio ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 07期

关键词：

ENANTIOSELECTIVE 1,6-CONJUGATE ADDITION; GRIGNARD-REAGENTS; CONJUGATE ADDITION; BORONIC ACIDS; ARYL; TETRAFLUOROBENZOBARRELENES; 1,4-ADDITION;

D O I：

10.1039/c2cc16973h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric addition of arylboroxines to delta-aryl-alpha,beta,gamma,delta-unsaturated ketones proceeded in the presence of an iridium catalyst coordinated with a chiral diene ligand to give high yields of delta-diaryl ketones with very high enantioselectivity.

引用

页码：973 / 975

页数：3

共 40 条

[31] Rhodium catalyzed asymmetric 1,4-addition of arylboronic acids to β,γ-unsaturated α-keto ester using chiral tert-butanesulfinylphosphines ligands
Wang, Juanjuan
Wang, Bing
Cao, Peng
Liao, Jian
TETRAHEDRON LETTERS, 2014, 55 (23) : 3450 - 3453
[32] 1,4-Addition of arylboronic acids to β-aryl-α,β-unsaturated ketones and esters catalyzed by a rhodium(I)-chiraphos complex for catalytic and enantioselective synthesis of selective endothelin -: A receptor antagonists
Itoh, Takahiro
Mase, Toshiaki
Nishikata, Takashi
Iyama, Tetsuji
Tachikawa, Hiroto
Kobayashi, Yuri
Yarnamoto, Yasunori
Miyaura, Norio
TETRAHEDRON, 2006, 62 (41) : 9610 - 9621
[33] Sodium Tetraarylborates as Effective Nucleophiles in Rhodium/Diene-Catalyzed 1,4-Addition to β,β-Disubstituted α,β-Unsaturated Ketones: Catalytic Asymmetric Construction of Quaternary Carbon Stereocenters
Shintani, Ryo
Tsutsumi, Yosuke
Nagaosa, Makoto
Nishimura, Takahiro
Hayashi, Tamio
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13588 - +
[34] Asymmetric Synthesis of Chiral Bicyclo[2.2.1]hepta-2,5-diene Ligands through Rhodium-Catalyzed Asymmetric Arylative Bis-cyclization of a 1,6-Enyne
Sun, Chao
Meng, He
Chen, Chen
Wei, Haili
Ming, Jialin
Hayashi, Tamio
ORGANIC LETTERS, 2021, 23 (16) : 6311 - 6315
[35] Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones
Yuan, Shuai
Zeng, Qingle
Wang, Jiajun
Zhou, Lihong
ARKIVOC, 2017, : 32 - 42
[36] Generation of chiral boron enolates by rhodium-catalyzed asymmetric 1,4-addition of 9-aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) to α,β-unsaturated ketones
Yoshida, K
Ogasawara, M
Hayashi, T
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05): : 1901 - 1905
[37] Chiral dihydrobenzofuran-based diphosphine (BICMAP): optical resolution and application to rhodium(I)-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to cyclic enones
Mino, Takashi
Hashimoto, Masatoshi
Uehara, Katsunori
Naruse, Yoshiaki
Kobayashi, Shohei
Sakamoto, Masami
Fujita, Tsutomu
TETRAHEDRON LETTERS, 2012, 53 (34) : 4562 - 4564
[38] Rhodium-Catalyzed Enantioselective Addition of Arylboroxines to Isatin-Derived N-Boc Ketimines Using Chiral Phosphite-Olefin Ligands: Asymmetric Synthesis of 3-Aryl-3-amino-2-oxindoles
Yu, Yue-Na
Qi, Wei-Yi
Wu, Chun-Yan
Xu, Ming-Hua
ORGANIC LETTERS, 2019, 21 (18) : 7493 - 7497
[39] Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions
Bieliunas, Vidmantas
Stoncius, Sigitas
CHEMCATCHEM, 2021, 13 (17) : 3815 - 3823
[40] ASYMMETRIC HYDROSILATION OF KETONES, CATALYZED BY RHODIUM COMPLEXES CONTAINING CHIRAL CHELATE LIGANDS - CRYSTAL AND MOLECULAR-STRUCTURE OF (BICYCLO[2.2.1]HEPTA-2,5-DIENE)[(S)-N,N-DIMETHYL-1-(ORTHO-(DIPHENYLARSINO)PHENYL)ETHYL-AMINE]RHODIUM(I) PERCHLORATE
PAYNE, NC
STEPHAN, DW
INORGANIC CHEMISTRY, 1982, 21 (01) : 182 - 188

← 1 2 3 4 →