Asymmetric NHC-Catalyzed Aza-Diels鈥揂lder Reactions: Highly Enantioselective Route to 伪-Amino Acid Derivatives and DFT Calculations

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• 作者：Limin Yang ; Fei Wang ; Richmond Lee ; Yunbo Lv ; Kuo-Wei Huang ; Guofu Zhong
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：August 1, 2014
• 年：2014
• 卷：16
• 期：15
• 页码：3872-3875
• 全文大小：282K
• ISSN：1523-7052

文摘

A facile N-heterocyclic carbene catalytic enantioselective aza-Diels鈥揂lder reaction of oxodiazenes with 伪-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations.