Transfer of axial chirality through the nickel-catalysed hydrocyanation of chiral allenes

被引:30
作者
Amako, Yuka [1 ]
Arai, Shigeru [1 ]
Nishida, Atsushi [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba, Japan
关键词
DYNAMIC KINETIC RESOLUTION; AEROBIC CONDITIONS; ALDEHYDES; RACEMIZATION; CYCLIZATION; COMPLEXES; PALLADIUM; MECHANISM; SILANES; ALKENES;
D O I
10.1039/c7ob00047b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The transfer of axial chirality of allenes is beginning to be exploited as a powerful method for creating central chirality, particularly through the use of transition metal catalysis. In this communication, the transfer of axial chirality of chiral allenes via nickel-catalysed hydrocyanation is achieved through both regio- and face-selective hydronickelation as well as regioselective reductive elimination. This protocol was applied to 12 substrates and gave chiral carbonitriles with up to 97% ee. Further application to hydrocyanative cyclization using a chiral allene-yne is also presented, along with a discussion of the corresponding mechanism of racemization.
引用
收藏
页码:1612 / 1617
页数:6
相关论文
共 31 条
[1]   Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes [J].
Amako, Yuka ;
Hori, Hiroto ;
Arai, Shigeru ;
Nishida, Atsushi .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) :10763-10775
[2]   A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes [J].
Arai, Shigeru ;
Hori, Hiroto ;
Amako, Yuka ;
Nishida, Atsushi .
CHEMICAL COMMUNICATIONS, 2015, 51 (35) :7493-7496
[3]   Hydrocyanative Cyclization and Three-Component Cross-Coupling Reaction between Allenes and Alkynes under Nickel Catalysis [J].
Arai, Shigeru ;
Amako, Yuka ;
Yang, Xiaofei ;
Nishida, Atsushi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) :8147-8150
[4]   Palladium-Catalyzed Cyanation of Nonactivated Alkynes; Development of Cyanopalladation and Its Application to Cyclization and Cycloaddition Reactions [J].
Arai, Shigeru ;
Nishida, Atsushi .
SYNLETT, 2012, (20) :2880-2893
[5]   Catalytic Dicyanative [4+2] Cycloaddition Triggered by Cyanopalladation of Conjugated Enynes under Aerobic Conditions [J].
Arai, Shigeru ;
Koike, Yuka ;
Hada, Hirohiko ;
Nishida, Atsushi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) :4522-+
[6]   Palladium-Catalyzed Cyanation of Carbon-Carbon Triple Bonds Under Aerobic Conditions [J].
Arai, Shigeru ;
Sato, Takashi ;
Koike, Yuka ;
Hayashi, Michino ;
Nishida, Atsushi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (25) :4528-4531
[7]   Ligand development in the Ni-catalyzed hydrocyanation of alkenes [J].
Bini, Laura ;
Muller, Christian ;
Vogt, Dieter .
CHEMICAL COMMUNICATIONS, 2010, 46 (44) :8325-8334
[8]   Mechanistic Studies on Hydrocyanation Reactions [J].
Bini, Laura ;
Muller, Christian ;
Vogt, Dieter .
CHEMCATCHEM, 2010, 2 (06) :590-608
[9]   Chemoenzymatic Dynamic Kinetic Resolution of Axially Chiral Allenes [J].
Deska, Jan ;
Ochoa, Carolina del Pozo ;
Backvall, Jan-E. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (15) :4447-4451
[10]   MECHANISTIC STUDIES OF NICKEL-CATALYZED ADDITION OF DCN AND H13CN TO PENTENENITRILES [J].
DRULINER, JD .
ORGANOMETALLICS, 1984, 3 (02) :205-208