Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates

被引：59

作者：

Chierchia, Matteo ^{[1
]}

Law, Chunyin ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, 2609 Beacon St, Chestnut Hill, MA 02467 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 39期

关键词：

asymmetric catalysis; boron; cross coupling; nickel; BORANE INTRAMOLECULAR COMPLEXES; VINYL BORONATE COMPLEXES; POTASSIUM T-BUTOXIDE; CONVENIENT PROCEDURE; ASYMMETRIC-SYNTHESIS; HECK REACTION; ATE COMPLEXES; ALPHA-OLEFINS; ALKYL-GROUPS; N-OXIDE;

D O I：

10.1002/anie.201706719

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic enantioselective conjunctive cross-coupling between 9-BBN borate complexes and aryl electrophiles can be accomplished with Ni salts in the presence of a chiral diamine ligand. The reactions furnish chiral 9-BBN derivatives in an enantioselective fashion and these are converted to chiral alcohols and amines, or engaged in other stereospecific C-C bond forming reactions.

引用

页码：11870 / 11874

页数：5

共 65 条

[1] Toward an understanding of the factors responsible for the 1,2-migration of alkyl groups in borate complexes
Aggarwal, VK
Fang, GY
Ginesta, X
Howells, DM
Zaja, M
[J]. PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 215 - 229
[2] [Anonymous], 2010, ANGEW CHEM, V122, P4360
[3] [Anonymous], 2017, ANGEW CHEM, V129, P804
[4] [Anonymous], 2007, ANGEW CHEM, V119, P7635
[5] [Anonymous], 2016, ANGEW CHEM, V128, P12100
[6] Conjunctive functionalization of vinyl boronate complexes with electrophiles: a diastereoselective three-component coupling
Armstrong, Roly J.
Sandford, Christopher
Garcia-Ruiz, Cristina
Aggarwal, Varinder K.
[J]. CHEMICAL COMMUNICATIONS, 2017, 53 (36) : 4922 - 4925
[7] Stereodivergent Olefination of Enantioenriched Boronic Esters
Armstrong, Roly J.
Garcia-Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (03) : 786 - 790
[8] Heck reaction using nickel/TPPTS catalyst and inorganic base on supported ethylene glycol phase
Bhanage, BH
Zhao, FY
Shirai, M
Arai, M
[J]. CATALYSIS LETTERS, 1998, 54 (04) : 195 - 198
[9] Asymmetric Synthesis of Allylsilanes by the Borylation of Lithiated Carbamates: Formal Total Synthesis of (-)-Decarestrictine D
Binanzer, Michael
Fang, Guang Yu
Aggarwal, Varinder K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (25) : 4264 - 4268
[10] NICKEL-CATALYZED COUPLING OF ACTIVATED ALKENES WITH ORGANIC HALIDES
BOLDRINI, GP
SAVOIA, D
TAGLIAVINI, E
TROMBINI, C
RONCHI, AU
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (03) : C62 - C64

← 1 2 3 4 5 6 7 →