-Amino Acids to Piperidinones by Petasis Methylenation and Acid-Induced Cyclization

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• 作者：Louis V. Adriaenssens ; Richard C. Hartley
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：December 21, 2007
• 年：2007
• 卷：72
• 期：26
• 页码：10287 - 10290
• 全文大小：69K
• 年卷期：v.72,no.26(December 21, 2007)
• ISSN：1520-6904

文摘

Ester-imine derivatives of -amino acids were methylenatedwith dimethyltitanocene under microwave irradiation and theresulting enol ethers cyclized with Brönsted acid or triisopropylaluminium to give 2,6-syn-disubstituted piperidinonesin good yield and diastereoselectivity. The method isanalogous to the Petasis-Ferrier rearrangement of 1,3-dioxan-4-ones to give tetrahydropyranones.