Palladium-catalyzed enantioselective conjugate addition of arylboronic acids

被引：140

作者：

Gini, F ^{[1
]}

Hessen, B ^{[1
]}

Minnaard, AJ ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst, Dept Organ Chem & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 23期

关键词：

D O I：

10.1021/ol052222d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric palladium-catalyzed conjugate addition of arylboronic acids to alpha,beta-unsaturated aldehydes, ketones, and esters is described. For cyclic substrates, excellent chemo-, regio-, and enantioselectivities are achieved when a Pd(O2CCF3)(2)/DuPHOS catalyst is applied.

引用

页码：5309 / 5312

页数：4

共 43 条

[1] Bonding modes in palladium(II) enolates:: Consequences for dynamic behavior and reactivity
Albéniz, AC
Catalina, NM
Espinet, P
Redón, R
[J]. ORGANOMETALLICS, 1999, 18 (26) : 5571 - 5576
[2] Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[3] Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids
Andappan, MMS
Nilsson, P
von Schenck, H
Larhed, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) : 5212 - 5218
[4] The first ligand-modulated oxidative Heck vinylation. Efficient catalysis with molecular oxygen as palladium(0) oxidant
Andappan, MMS
Nilsson, P
Larhed, M
[J]. CHEMICAL COMMUNICATIONS, 2004, (02) : 218 - 219
[5] High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites
Boiteau, JG
Minnaard, AJ
Feringa, BL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9481 - 9484
[6] Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands
Boiteau, JG
Imbos, F
Minnaard, AJ
Feringa, BL
[J]. ORGANIC LETTERS, 2003, 5 (05) : 681 - 684
[7] Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands (vol 5, pg 682, 2003)
Boiteau, JG
Imbos, R
Minnaard, AJ
Feringa, BL
[J]. ORGANIC LETTERS, 2003, 5 (08) : 1385 - 1385
[8] Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors
Defieber, C
Paquin, JF
Serna, S
Carreira, EM
[J]. ORGANIC LETTERS, 2004, 6 (21) : 3873 - 3876
[9] Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes
Denmark, SE
Amishiro, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 6997 - 7003
[10] First examples of improved catalytic asymmetric C-C bond formation using the monodentate ligand combination approach
Duursma, A
Hoen, R
Schuppan, J
Hulst, R
Minnaard, AJ
Feringa, BL
[J]. ORGANIC LETTERS, 2003, 5 (17) : 3111 - 3113

← 1 2 3 4 5 →