Isothiourea-Mediated Asymmetric Functionalization of 3-Alkenoic Acids

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• 作者：Louis C. Morrill ; Samuel M. Smith ; Alexandra M. Z. Slawin ; Andrew D. Smith
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：February 21, 2014
• 年：2014
• 卷：79
• 期：4
• 页码：1640-1655
• 全文大小：691K
• ISSN：1520-6904

文摘

Isothiourea HBTM-2.1 promotes the catalytic asymmetric 伪-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.