Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

被引：27

作者：

Cui, Yi ^{[1
]}

Yamashita, Yasuhiro ^{[1
]}

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 83期

基金：

日本学术振兴会;

关键词：

CATALYTIC ENANTIOSELECTIVE ALLYLATION; ASYMMETRIC ALLYLBORATION; KETONES; ACID; REAGENTS; HALIDES; BOND; CROTYLATION; REACTIVITY; ALDEHYDES;

D O I：

10.1039/c2cc34340a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.

引用

页码：10319 / 10321

页数：3

共 47 条

[1]

Alvaro G, 2002, SYNLETT, P651

[2] Diene-Ligated Iridium Catalyst for Allylation Reactions of Ketones and Imines [J].

Barker, Timothy J. ;

Jarvo, Elizabeth R. .

ORGANIC LETTERS, 2009, 11 (05) :1047-1049

[3] The Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral Biphenols [J].

Barnett, David S. ;

Moquist, Philip N. ;

Schaus, Scott E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8679-8682

[4] ADDITION AT TRIPLE BOND OF ORGANOZINC COMPOUNDS ISSUED FROM ALPHA-ACETYLENIC BROMIDES - SYNTHESIS OF BETA-ENYNE AND BETA-ENYNOL [J].

BELLASSOUED, M ;

FRANGIN, Y ;

GAUDEMAR, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 166 (01) :1-8

[5] Two syntheses of (-)-kainic acid via highly stereoselective zinc-ene cyclizations [J].

Chalker, Justin M. ;

Yang, Ao ;

Deng, Kai ;

Cohen, Theodore .

ORGANIC LETTERS, 2007, 9 (19) :3825-3828

[6]

Crabtree RH, 2005, ORGANOMETALLIC CHEMISTRY OF THE TRANSITION METALS, 4TH EDITION, P1, DOI 10.1002/0471718769

[7] Catalytic, Nucleophilic Allylation of Aldehydes with Allyl Acetate [J].

Denmark, Scott E. ;

Nguyen, Son T. .

ORGANIC LETTERS, 2009, 11 (03) :781-784

[8] Diastereoselective allylation and crotylation of N-unsubstituted imines derived from ketones [J].

Dhudshia, B ;

Tiburcio, J ;

Thadani, AN .

CHEMICAL COMMUNICATIONS, 2005, (44) :5551-5553

[9] Asymmetric addition of allylic nucleophiles to imino compounds [J].

Ding, H ;

Friestad, GK .

SYNTHESIS-STUTTGART, 2005, (17) :2815-2829

[10] Mild and General Zinc-Alkoxide-Catalyzed Allylations of Ketones with Allyl Pinacol Boronates [J].

Fandrick, Keith R. ;

Fandrick, Daniel R. ;

Gao, Joe J. ;

Reeves, Jonathan T. ;

Tan, Zhulin ;

Li, Wenjie ;

Song, Jinhua J. ;

Lu, Bruce ;

Yee, Nathan K. ;

Senanayake, Chris H. .

ORGANIC LETTERS, 2010, 12 (17) :3748-3751

← 1 2 3 4 5 →