Asymmetric allylboration of ketones catalyzed by chiral diols

被引：219

作者：

Lou, Sha ^{[1
]}

Moquist, Philip N. ^{[1
]}

Schaus, Scott E. ^{[1
]}

机构：

[1] Boston Univ, Ctr Clin Methodol & Lib Dev, Dept Chem, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 39期

关键词：

D O I：

10.1021/ja0651308

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of ketones. The reaction requires 15 mol % of 3,3′-Br2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (76-93%) and high enantiomeric ratios (95:5-99.5:0.5). High diastereoselectivities (dr ≥ 98:2) and enantioselectivities (er ≥ 98:2) are obtained in the reactions of acetophenone with crotyldiisopropoxyboranes. Copyright © 2006 American Chemical Society.

引用

页码：12660 / 12661

页数：2

共 28 条

[1] The enantioselective allylation and crotylation of sterically hindered and functionalized aryl ketones: Convenient access to unusual tertiary carbinol structures [J].

Burns, Noah Z. ;

Hackman, Blaine M. ;

Ng, Pui Yee ;

Powelson, Ian A. ;

Leighton, James L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3811-3813

[2] B-allyl-10-Ph-9-borabicyclo[3.3.2]decanes:: Strategically designed for the asymmetric allylboration of ketones [J].

Canales, E ;

Prasad, KG ;

Soderquist, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11572-11573

[3] BINOL-Ti-catalyzed synthesis of tertiary homoallylic alcohols: The first catalytic asymmetric allylation of ketones [J].

Casolari, S ;

D'Addario, D ;

Tagliavini, E .

ORGANIC LETTERS, 1999, 1 (07) :1061-1063

[4]

Cunningham A, 2002, SYNLETT, P43

[5]

Denmark S. E., 2000, MODERN CARBONYL CHEM, P299

[6] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

[7] ACYLOXYBORANE - AN ACTIVATING DEVICE FOR CARBOXYLIC-ACIDS [J].

FURUTA, K ;

MIWA, Y ;

IWANAGA, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6254-6255

[8]

Girard C, 1998, ANGEW CHEM INT EDIT, V37, P2923, DOI 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO

[9]

2-1

[10] Acceleration effect of Lewis acid in allylboration of aldehydes: Catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols [J].

Ishiyama, T ;

Ahiko, T ;

Miyaura, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (42) :12414-12415

← 1 2 3 →