Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

被引：95

作者：

Li, Hui ^{[1
]}

Zhang, Fu-Min ^{[1
]}

Tu, Yong-Qiang ^{[1
]}

Zhang, Qing-Wei ^{[1
]}

Chen, Zhi-Min ^{[1
]}

Chen, Zhi-Hua ^{[1
]}

Li, Jian ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 09期

关键词：

HIGHLY EFFICIENT SYNTHESIS; RING EXPANSION; ASYMMETRIC BROMOLACTONIZATION; HYDROXY EPOXIDES; BRONSTED ACID; STEREOSELECTIVE CONSTRUCTION; SEMIPINACOL REARRANGEMENT; ALLYLIC ALCOHOLS; BROMINATION; CATALYSIS;

D O I：

10.1039/c1sc00295c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A bromination/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. With 5 mol% (DHQD)(2)PYDZ, beta-bromoketones containing an all-alpha-carbon quaternary center, which were synthetically useful but challenging to construct, were obtained in up to 97% yield and 93% ee.

引用

页码：1839 / 1841

页数：3

共 59 条

[1]

ANDREW AM, 2001, ORG LETT, V3, P2049

[2] Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Melchiorre, P ;

Sambri, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6219-6222

[3] Organocatalytic Formation of Quaternary Stereocenters [J].

Bella, Marco ;

Gasperi, Tecla .

SYNTHESIS-STUTTGART, 2009, (10) :1583-1614

[4] Organocatalytic asymmetric α-bromination of aldehydes and ketones [J].

Bertelsen, S ;

Halland, N ;

Bachmann, S ;

Marigo, M ;

Braunton, A ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (38) :4821-4823

[5] Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives [J].

Cai, Yunfei ;

Liu, Xiaohua ;

Hui, Yonghai ;

Jiang, Jun ;

Wang, Wentao ;

Chen, Weiliang ;

Lin, Lili ;

Feng, Xiaoming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) :6160-6164

[6] Enantioselective Halocyclization Reactions for the Synthesis of Chiral Cyclic Compounds [J].

Chen, Guofei ;

Ma, Shengming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) :8306-8308

[7] A highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids [J].

Chen, YG ;

Tian, SK ;

Deng, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9542-9543

[8] Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones [J].

Chen, Zhi-Min ;

Zhang, Qing-Wei ;

Chen, Zhi-Hua ;

Li, Hui ;

Tu, Yong-Qiang ;

Zhang, Fu-Min ;

Tian, Jin-Miao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (23) :8818-8821

[9] Stereoselective construction of quaternary stereocenters [J].

Christoffers, J ;

Baro, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482

[10]

Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858

← 1 2 3 4 5 6 →