Asymmetric Synthesis of Spiro-epoxyoxindoles by the Catalytic Darzens Reaction of Isatins with Phenacyl Bromides
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- 作者：Yulong Kuang ; Yan Lu ; Yu Tang ; Xiaohua Liu ; Lili Lin ; Xiaoming Feng
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：August 15, 2014
- 年：2014
- 卷：16
- 期：16
- 页码：4244-4247
- 全文大小：308K
- ISSN：1523-7052
文摘
The asymmetric Darzens reaction between phenacyl bromides and N-protected isatins was developed to synthesize potentially bioactive spiro-epoxyoxindoles. The optically active products were obtained in moderate to good yields and enantioselectivities catalyzed by chiral N,N鈥?dioxide-Co(acac)2 complexes. A retro-aldol process accompanying the ring-closure step was observed in the process. A chiral control step was determined to be the initial aldol addition.