Ln(OTf)3-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols

被引:9
作者
Nakamura, Daichi [1 ]
Sasano, Yusuke [1 ]
Iwabuchi, Yoshiharu [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi, Japan
关键词
ASYMMETRIC EPOXIDATION; ALLYLIC ALCOHOLS; ENANTIOSELECTIVE EPOXIDATION; NUCLEOPHILIC OPENINGS; BETA-CYCLODEXTRIN; EFFICIENT; EPOXYALCOHOLS; DERIVATIVES; AMINOLYSIS; STRATEGIES;
D O I
10.1039/c8ob02448k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselectivity of Ln(OTf)(3)-catalysed alcoholysis of 2,3- and 3,4-epoxy alcohols was closely investigated to expand the scope of the transformations. The synthetic use was demonstrated by application to the construction of 4-propoxy-5-hydroxy-2,3-pentanedione (C4-propoxy-HPD), which is a potent synthetic mediator in AI-2 quorum sensing.
引用
收藏
页码:3581 / 3589
页数:9
相关论文
共 24 条
[21]   Regio- and Enantioselective Epoxy Ring Opening of 2,3-Epoxy-3-phenyl Alcohols/Carboxylic Acids and Their Derivatives [J].
Zhan, Xiaoyan ;
Du, Xi .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (04) :679-692
[22]   Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives [J].
Huang, Tianyu ;
Lin, Lili ;
Hu, Xiaolei ;
Zheng, Jianfeng ;
Liu, Xiaohua ;
Feng, Xiaoming .
CHEMICAL COMMUNICATIONS, 2015, 51 (57) :11374-11377
[23]   2-Amino homopropargyl alcohols from the highly regioselective Ag2CO3-catalyzed nucleophilic openings of alkynyl epoxides by amines [J].
Yang, Jianlin ;
Zhang, Ming ;
Wang, Peng ;
Liu, Wenjuan ;
Shen, Ruwei .
CHINESE CHEMICAL LETTERS, 2018, 29 (03) :524-526
[24]   Zn(OTf)2-Catalyzed Formal [3+3] Cascade Annulation of Propargylic Alcohols with 2-Aminochromones: Accessing the Chromeno[2,3-b]pyridines [J].
Tong, Pei ;
Sun, Zhou ;
Wang, Shutao ;
Zhang, Yuan ;
Li, Ying .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21) :13967-13974