Catalytic Enantioselective Intermolecular Desymmetrization of 3-Substituted Oxetanes

被引：98
作者：
Wang, Zhaobin [1 ]
Chen, Zhilong [1 ]
Sun, Jianwei [1 ]
机构：
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 26期
关键词：
asymmetric catalysis; nucleophilic addition; organocatalysis; strained molecules; sulfur; RING EXPANSION; ASYMMETRIC EPOXIDATION; ACID; OXIDATION; OXIRANE; OLEFINS;
D O I：
10.1002/anie.201300188
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Wring it out: The title reaction proceeds in the presence of chiral Brønsted acid catalysts. This efficient ring-opening process features low catalyst loading, mild reaction conditions, broad functional group compatibility, high enantioselectivity, and the capability to generate chiral quaternary centers. The highly functionalized desymmetrization products are versatile chiral building blocks in organic synthesis. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：6685 / 6688
页数：4
相关论文
共 64 条
[1]  
Adair G, 2008, ALDRICHIM ACTA, V41, P31
[2]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[3]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[4]  
[Anonymous], 2008, ANGEW CHEM INT ED, V47, P248
[5]  
[Anonymous], 2013, ANGEW CHEM INT ED, V52, P2027
[6]  
[Anonymous], 2006, ANGEW CHEM INT ED, V45, P7736
[7]  
[Anonymous], 2001, ANGEW CHEM INT ED, V40, P4591
[8]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P5675
[9]  
[Anonymous], 2010, ANGEW CHEM INT ED, V49, P9052
[10]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P1677
1234567