Activation of functional arylzincs prepared from aryl iodides and highly enantioselective addition to aldehydes

被引：41

作者：

DeBerardinis, Albert M. ^{[1
]}

Turlington, Mark ^{[1
]}

Pu, Lin ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 13期

关键词：

D O I：

10.1021/ol8008478

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easily available chiral ligand (S)-1 is found to activate the nucleophilic reaction of the arylzincs prepared in situ from the reaction of aryl iodides with Et2Zn. Both high yields and high enantioselectivity (up to >99% ee) for the reaction of these arylzincs with a variety of aldehydes are obtained. The mild reaction conditions and the good functional group tolerance make this catalytic asymmetric process synthetically useful.

引用

页码：2709 / 2712

页数：4

共 50 条

[41] Highly enantioselective addition of diethylzinc to aldehydes catalyzed by isoindolinyl alcohol as a chiral ligand
Park, DH
Choi, HJ
Lee, S
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (11) : 1559 - 1560
[42] Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water
Zhu, Shaolin
Yu, Shouyun
Ma, Dawei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) : 545 - 548
[43] Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes
Wang, W
Wang, J
Li, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) : 1369 - 1371
[44] Highly enantioselective catalytic methyl propiolate addition to both aromatic and aliphatic aldehydes
Huang, Jian
Wei, Siping
Wang, Li
Zhang, Chun
Li, Shuangxun
Liu, Pingxian
Du, Xi
Wang, Qin
TETRAHEDRON-ASYMMETRY, 2016, 27 (9-10) : 428 - 435
[45] Computer assisted design: Ligands for highly enantioselective addition of diethyl zinc to aldehydes
Pericas, MA
Vidal-Ferran, A
Sola, L
Reddy, KS
Vazquez, A
Moyano, A
Riera, A
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U511 - U511
[46] ENANTIOSELECTIVE ADDITION OF ARYL GROUPS TO AROMATIC-ALDEHYDES USING CHIRAL ARYLTITANIUM BINAPHTHOL DERIVATIVES
SEEBACH, D
BECK, AK
ROGGO, S
WONNACOTT, A
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (09): : 3673 - 3682
[47] Rh(III)-Catalyzed Enantioselective Intermolecular Aryl C-H Bond Addition to Aldehydes
Wu, Zhi-Jie
Wu, Zhuo
Zhang, Wen-Wen
Gu, Qing
You, Shu-Li
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (23) : 2780 - 2784
[48] Catalytic enantioselective aryl transfer:: asymmetric addition of boronic acids to aldehydes using pyrrolidinylmethanols as ligands
Braga, AL
Lüdtke, DS
Schneider, PH
Vargas, F
Schneider, A
Wessjohann, LA
Paixao, MW
TETRAHEDRON LETTERS, 2005, 46 (45) : 7827 - 7830
[49] Gold-Carbon Contacts from Oxidative Addition of Aryl Iodides
Starr, Rachel L.
Fu, Tianren
Doud, Evan A.
Stone, Ilana
Roy, Xavier
Venkataraman, Latha
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (15) : 7128 - 7133
[50] Catalytic enantioselective reactions .6. A new chiral catalyst for highly enantioselective addition of diethylzinc to aliphatic aldehydes
Cho, BT
Kim, N
Khoo, JH
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1996, 17 (01) : 1 - 2

← 1 2 3 4 5 →