Enantioselective Palladium-Catalyzed Oxidative Cascade Cyclization of Aliphatic Alkenyl Amides

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• 作者：Wei Du ; Qiangshuai Gu ; Yang Li ; Zhenyang LinDan Yang
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：19
• 期：2
• 页码：316-319
• 全文大小：402K
• ISSN：1523-7052

文摘

The catalyst system of Pd(TFA)₂/(S,S)-diPh-pyrox is reported to promote the highly efficient enantioselective oxidative cascade cyclization of alkene-tethered aliphatic acrylamides under mild aerobic conditions. A series of pyrrolizidine derivatives have been synthesized in good yield and excellent enantioselectivity. Deuterium-labeling experiments have revealed that the reaction proceeded through an anti-aminopalladation (anti-AP) pathway with high selectivity. The transition states for the anti-AP step have been calculated to account for the observed enantioselectivity.