Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Racemic Secondary Allylic Alcohols through Kinetic Resolution

被引：8
作者：
Suzuki, Shunsuke [1 ]
Shibata, Yu [1 ]
Tanaka, Ken [1 ]
机构：
[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528550, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 17期
关键词：
allylic alcohols; asymmetric [2+2+2] cycloaddition; enynes; kinetic resolution; rhodium; BAYLIS-HILLMAN ADDUCTS; 2 DIFFERENT ALKYNES; ENANTIOSELECTIVE SYNTHESIS; COMPLEXES; ISOMERIZATION; CONSTRUCTION; CYCLIZATION; ALKENE; REGIO;
D O I：
10.1002/chem.202000010
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
It has been established that a cationic rhodium(I)/P-phos complex catalyzes the asymmetric [2+2+2] cycloaddition of 1,6-enynes with racemic secondary allylic alcohols to produce the corresponding chiral bicyclic cyclohexenes, possessing three stereogenic centers, as a single diastereomer with excellent ee values. Mechanistic experiments revealed that the present cycloaddition proceeds through the kinetic resolution of the racemic secondary allylic alcohols, in which one enantiomer preferentially reacts with the 1,6-enyne.
引用
收藏
页码：3698 / 3702
页数：5
相关论文
共 53 条
[1]   Recent Advances in Stereoselective [2+2+2] Cycloadditions [J].
Amatore, Muriel ;
Aubert, Corinne .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (02) :265-286
[2]  
[Anonymous], 2015, ANGEW CHEM, V127, P8359
[3]   Alkenes in [2+2+2] Cycloadditions [J].
Dominguez, Gema ;
Perez-Castells, Javier .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) :6720-6739
[4]   Recent advances in [2+2+2] cycloaddition reactions [J].
Dominguez, Gema ;
Perez-Castells, Javier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3430-3444
[5]   Regio- and enantioselective intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with methyl arylpropiolates [J].
Evans, PA ;
Lai, KW ;
Sawyer, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12466-12467
[6]   Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds [J].
Fernandez, Marti ;
Parera, Magda ;
Parella, Teodor ;
Lledo, Agusti ;
Le Bras, Jean ;
Muzart, Jacques ;
Pla-Quintana, Anna ;
Roglans, Anna .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (11) :1848-1853
[7]  
Hara J., 2014, ANGEW CHEM, V126, P3000, DOI DOI 10.1002/ANGE.201310336
[8]   Highly Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Cross-Cyclotrimerization of Two Different Alkynes with Alkenes [J].
Hara, Jun ;
Ishida, Mana ;
Kobayashi, Masayuki ;
Noguchi, Keiichi ;
Tanaka, Ken .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (11) :2956-2959
[9]   Rhodium-Catalyzed Enantioconvergent Isomerization of Homoallylic and Bishomoallylic Secondary Alcohols [J].
Huang, Rui-Zhi ;
Lau, Kai Kiat ;
Li, Zhaofeng ;
Liu, Tang-Lin ;
Zhao, Yu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (44) :14647-14654
[10]   Rhodium-Catalyzed Asymmetric [2+2+2] Cyclization of 1,6-Enynes and Aldehydes [J].
Ishida, Mana ;
Shibata, Yu ;
Noguchi, Keiichi ;
Tanaka, Ken .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12578-12581
123456