Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes

被引：126

作者：

Brown, MK ^{[1
]}

Degrado, SJ ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 33期

关键词：

asymmetric catalysis; conjugate addition; copper; enantioselectivity; zinc;

D O I：

10.1002/anie.200501251

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The first generally effective method for catalytic asymmetric conjugate addition (ACA) of dialkylzinc reagents to unsaturated furanones and pyranones (see scheme) with different steric and electronic properties is reported. Synthesis, isolation, and characterization of catalytically active and air-stable chiral Cu-peptide complexes are also described. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5306 / 5310

页数：5

共 45 条

[1] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions
Alexakis, A
Benhaim, C
Rosse, S
Humam, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) : 5262 - 5263
[2] Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[3] Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal
Arnold, LA
Naasz, R
Minnaard, AJ
Feringa, BL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) : 5841 - 5842
[4] Cesati RR, 2004, J AM CHEM SOC, V126, P96
[5] Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes
Choi, H
Hua, ZH
Ojima, I
[J]. ORGANIC LETTERS, 2004, 6 (16) : 2689 - 2691
[6] 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
[7] Efficient cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones
Degrado, SJ
Mizutani, H
Hoveyda, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13362 - 13363
[8] Modular peptide-based phosphine ligands-in asymmetric catalysis: Efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones
Degrado, SJ
Mizutani, H
Hoveyda, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) : 755 - 756
[9] Enantioselective Cu-catalyzed conjugate addition of diethylzinc to acyclic aliphatic enones
Duncan, AP
Leighton, JL
[J]. ORGANIC LETTERS, 2004, 6 (22) : 4117 - 4119
[10] Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes:: A catalytic route to β2-amino acids, aldehydes, and alcohols
Duursma, A
Minnaard, AJ
Feringa, BL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) : 3700 - 3701

← 1 2 3 4 5 →