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

页码：5519 / 5527

页数：9

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