Ligand-Controlled Stereodivergent, Enantioselective Conjugate Addition of 2-Oxazoline- and 2-Thiazoline-4-carboxylate to Nitroalkene Catalyzed by Chiral Copper Complexes
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- 作者：Yukiko Matsuda ; Akihiro Koizumi ; Ryosuke Haraguchi ; Shin-ichi Fukuzawa
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：September 2, 2016
- 年：2016
- 卷：81
- 期：17
- 页码：7939-7944
- 全文大小：255K
- 年卷期：0
- ISSN：1520-6904
文摘
The copper-catalyzed asymmetric conjugate addition of 2-oxazoline- and 2-thiazoline-4-carboxylate to a nitroalkene proceeded to give either the syn or anti adduct selectively in high enantiomeric excess when an appropriate chiral ligand was used. Subsequent reduction of the nitro group followed by hydrolysis of the oxazoline ring yielded an optically active γ-lactam of protected α-quaternary serine derivative.