Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane

被引：128

作者：

Guo, Jun ^{[1
]}

Chen, Jianhui ^{[1
]}

Lu, Zhan ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 26期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE BOROHYDRIDE REDUCTION; ALKENE HYDROBORATION; HYDROSILYLATION; IRON; CARBONYL; HYDROGENATION; COMPLEXES; ALKYNES; BORANE; CHEMO;

D O I：

10.1039/c5cc01084e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly enantioselective cobalt-catalyzed hydroboration reaction of aryl ketones with HBpin was developed using iminopyridine oxazoline ligands. Halides, amines, ethers, sulfides, esters and amides are well tolerated under the mild reaction conditions, demonstrating its synthetic advantage. Substituted diaryl ketones could also be hydroborated with high enantioselectivity.

引用

页码：5725 / 5727

页数：3

共 66 条

[31] Iron- and Cobalt-Catalyzed Asymmetric Hydrosilylation of Ketones and Enones with Bis(oxazolinylphenyl)amine Ligands [J].

Inagaki, Tomohiko ;

Phong, Le Thanh ;

Furuta, Akihiro ;

Ito, Jun-ichi ;

Nishiyama, Hisao .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (10) :3090-3096

[32] ASYMMETRIC-SYNTHESIS USING CHIRALLY MODIFIED BOROHYDRIDES .3. ENANTIOSELECTIVE REDUCTION OF KETONES AND OXIME ETHERS WITH REAGENTS PREPARED FROM BORANE AND CHIRAL AMINO-ALCOHOLS [J].

ITSUNO, S ;

NAKANO, M ;

MIYAZAKI, K ;

MASUDA, H ;

ITO, K ;

HIRAO, A ;

NAKAHAMA, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10) :2039-2044

[33] Stoichiometric and catalytic B-C bond formation from unactivated hydrocarbons and boranes [J].

Iverson, CN ;

Smith, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7696-7697

[34] Asymmetric hydrogenation of prochiral amino ketones to amino alcohols for pharmaceutical use [J].

Klingler, Franz Dietrich .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1367-1376

[35] Catalytic enantioselective borohydride reduction of ortho-fluorinated benzophenones [J].

Kokura, Ai ;

Tanaka, Saiko ;

Ikeno, Taketo ;

Yamada, Tohru .

ORGANIC LETTERS, 2006, 8 (14) :3025-3027

[36] A Boron-Substituted Analogue of the Shvo Hydrogenation Catalyst: Catalytic Hydroboration of Aldehydes, Imines, and Ketones [J].

Koren-Selfridge, Liza ;

Londino, Hannah N. ;

Vellucci, Jessica K. ;

Simmons, Bryan J. ;

Casey, Charles P. ;

Clark, Timothy B. .

ORGANOMETALLICS, 2009, 28 (07) :2085-2090

[37] Asymmetric hydrosilylation, transfer hydrogenation and hydrogenation of ketones catalyzed by iridium complexes [J].

Malacea, Raluca ;

Poli, Rinaldo ;

Manoury, Eric .

COORDINATION CHEMISTRY REVIEWS, 2010, 254 (5-6) :729-752

[38] ASYMMETRIC REDUCTIONS WITH ORGANOBORANE REAGENTS [J].

MIDLAND, MM .

CHEMICAL REVIEWS, 1989, 89 (07) :1553-1561

[39] Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates [J].

Murata, M ;

Oyama, T ;

Watanabe, S ;

Masuda, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :164-168

[40] ENANTIOSELECTIVE REDUCTION OF KETONES WITH SODIUM-BOROHYDRIDE, CATALYZED BY OPTICALLY-ACTIVE (BETA-OXOALDIMINATO)COBALT(II) COMPLEXES [J].

NAGATA, T ;

YOROZU, K ;

YAMADA, T ;

MUKAIYAMA, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (19) :2145-2147

← 1 2 3 4 5 6 7 →