Highly enantioselective aryl additions of [AlAr3(thf)] to ketones catalyzed by a Titanium(IV) catalyst of (S)-Binol

被引：82

作者：

Chen, Chien-An ^{[1
]}

Wu, Kuo-Hui ^{[1
]}

Gau, Han-Mou ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 28期

关键词：

aluminum; asymmetric synthesis; homogeneous catalysis; ketones; titanium;

D O I：

10.1002/anie.200701201

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Chiral transfer: Novel asymmetric aryl transfers from [AlAr3(thf)] to a wide variety of ketones are catalyzed by an in situ generated titanium species with (S)-binol as the chiral ligand. The reaction affords tertiary alcohols with enantioselectivities up to 97% ee (see scheme). Binol = 2,2′-dihydroxy-1,1′-binaphthyl. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5373 / 5376

页数：4

共 70 条

[1] Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium - BINOLate species
Balsells, J
Davis, TJ
Carroll, P
Walsh, PJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10336 - 10348
[2] Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes
Biswas, K
Prieto, O
Goldsmith, PJ
Woodward, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) : 2232 - 2234
[3] Biswas K., 2005, ANGEW CHEM, V117, P2272
[4] BINOL: A versatile chiral reagent
Brunel, JM
[J]. CHEMICAL REVIEWS, 2005, 105 (03) : 857 - 897
[5] The enantioselective allylation and crotylation of sterically hindered and functionalized aryl ketones: Convenient access to unusual tertiary carbinol structures
Burns, Noah Z.
Hackman, Blaine M.
Ng, Pui Yee
Powelson, Ian A.
Leighton, James L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) : 3811 - 3813
[6] BURNS NZ, 2006, ANGEW CHEM, V118, P3895
[7] B-allyl-10-Ph-9-borabicyclo[3.3.2]decanes:: Strategically designed for the asymmetric allylboration of ketones
Canales, E
Prasad, KG
Soderquist, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) : 11572 - 11573
[8] Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes
Chan, ASC
Zhang, FY
Yip, CW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) : 4080 - 4081
[9] Low ligand loading, highly enantioselective addition of phenylacetylene to aromatic ketones catalyzed by Schiff-base amino alcohols
Chen, Chao
Hong, Liang
Xu, Zhao-Qing
Liu, Lei
Wang, Rui
[J]. ORGANIC LETTERS, 2006, 8 (11) : 2277 - 2280
[10] Couladouros E. A., 2002, ANGEW CHEM, V114, P3829

← 1 2 3 4 5 6 7 →