Rhodium-Catalyzed Asymmetric 1,4-Addition of Heteroaryl Cyclic Triolborate to α,β-Unsaturated Carbonyl Compounds

被引：33

作者：

Yu, Xiao-Qiang ^{[1
]}

Yamamoto, Yasunori ^{[1
]}

Miyaura, Norio ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

来源：

SYNLETT | 2009年 / 06期

关键词：

heteroaryl cyclic triolborate; rhodium catalyst; asymmetric reaction; conjugate addition; ENANTIOSELECTIVE CONJUGATE ADDITION; ARYLBORONIC ACIDS; ENONES; ARYL; LIGANDS; ESTERS; COMPLEXES; EFFICIENT; DIETHYLZINC; REAGENTS;

D O I：

10.1055/s-0028-1088198

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed asymmetric 1,4-additions of electron-deficient heteroaryl groups to alpha,beta-unsaturated carbonyl compounds were established. The reaction resulted in very low yields due to competitive C-B bond cleavage when arylboronic acids. their pinacol esters, or potassium trifluoroborates were used. However, the corresponding lithium heteroaryl(triol)borates afforded 1,4-adducts With high enantioselectivities up to 97% in the presence of a rhodium(I) catalyst chelated with a chiral BINAP or BIPAM ligand.

引用

页码：994 / 998

页数：5

共 50 条

[21] Chiral bis-phosphoramidites based on linked-BINOL for rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds
Yamamoto, Y
Kurihara, K
Sugishita, N
Oshita, K
Piao, DG
Miyaura, N
CHEMISTRY LETTERS, 2005, 34 (09) : 1224 - 1225
[22] Rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated amides
Sakuma, S
Miyaura, N
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26): : 8944 - 8946
[23] Rhodium-catalyzed asymmetric 1,4-addition of α,β-unsaturated imino esters using chiral bicyclic bridgehead phosphoramidite ligands
Kim, Hyunwoo
Lee, Ansoo
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[24] Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands
Lee, Ansoo
Kim, Hyunwoo
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (35) : 11250 - 11253
[25] Rhodium-catalyzed asymmetric 1,4-addition of 2-alkenyl-1,3,2-benzodioxaboroles to α,β-unsaturated ketones
Takaya, Y
Ogasawara, M
Hayashi, T
TETRAHEDRON LETTERS, 1998, 39 (46) : 8479 - 8482
[26] Rhodium-catalyzed asymmetric 1,4-addition.
Hayashi, T
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B195 - B195
[27] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine
Chen, G
Tokunaga, N
Hayashi, T
ORGANIC LETTERS, 2005, 7 (11) : 2285 - 2288
[28] Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds
Tato, Ruben
Riveiros, Ricardo
Perez Sestelo, Jose
Sarandeses, Luis A.
TETRAHEDRON, 2012, 68 (05) : 1606 - 1611
[29] Chiral Heterodisulfoxide Ligands in Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Chromenones
Han, Fuzhong
Chen, Guihua
Zhang, Xiangyang
Liao, Jian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (16) : 2928 - 2931
[30] Planar-chiral cyrhetrenes for the rhodium-catalyzed asymmetric 1,4-addition and the hydrogenation of enamides
Stemmler, RT
Bolm, C
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24): : 9925 - 9931

← 1 2 3 4 5 →