Pauson鈥揔hand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones

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• 作者：Nuria Aiguabella ; Albert Pesquer ; Xavier Verdaguer ; Antoni Riera
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：June 7, 2013
• 年：2013
• 卷：15
• 期：11
• 页码：2696-2699
• 全文大小：293K
• 年卷期：v.15,no.11(June 7, 2013)
• ISSN：1523-7052

文摘

A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson鈥揔hand (PK) reaction of norbornadiene and N-Boc-propargylamine as an alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the 伪 side chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.