Enantioselective Synthesis of N-PMP-1,2-dihydropyridines via Formal [4 + 2] Cycloaddition between Aqueous Glutaraldehyde and Imines

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• 作者：Panduga Ramaraju ; Nisar A. Mir ; Deepika Singh ; Vivek K. Gupta ; Rajni Kant ; Indresh Kumar
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 20, 2015
• 年：2015
• 卷：17
• 期：22
• 页码：5582-5585
• 全文大小：400K
• ISSN：1523-7052

文摘

A simple and highly practical one-pot formal [4 + 2] cycloaddition approach for the enantioselective synthesis of N-PMP-1,2-dihydropyridines (DHPs) is described. This chemistry involves an amino-catalytic direct Mannich reaction/cyclization followed by IBX-mediated chemo- and regioselective oxidation sequence between readily available aqueous glutaraldehyde and imines under very mild conditions. A series of N-PMP-1,2-DHPs have been prepared in high yields and excellent enantioselectivity. This method also gives access to both enantiomers of 1,2-DHPs in surplus amount by shifting the catalyst configuration.