Catalytic and highly enantioselective reactions of α-sulfonyl carbanions with chiral bis(oxazoline)s

被引：23
|
作者：
Nakamura, Shuichi [1 ]
Hirata, Norimune [1 ]
Yamada, Ryusuke [1 ]
Kita, Takeshi [1 ]
Shibata, Norio [1 ]
Toru, Takeshi [1 ]
机构：
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 18期
关键词：
asymmetric synthesis; carbanions; catalysis; chirality; enantioselectivity;
D O I：
10.1002/chem.200800221
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The enantioselective reactions of lithiated benzyl trifluoromethyl sultones with a substoichiometric amount of a bis(oxazoline) and various aldehydes is disclosed. The products were formed with excellent diastereo- and enantioselectivities. Fluorination of the sulfone with N-fluorobenzenesulfonimide and a stoichiometric amount of a bis(oxazoline) gave products with extremely high enantioselectivities (up to 99% ee; ee = enantiomeric excess). The enantioselective reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.
引用
收藏
页码：5519 / 5527
页数：9
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