Addition reaction of benzylbenzylidenenamine to lithium enolates of 1,3-dioxolan-4-one: synthesis of 2-phenylisoserines

作者：Juarez Guerra Lizbeth; Rojas Lima Susana^*; Lopez Ruiz Heraclio

来源：ARKIVOC, 2011, 354-366.

• 2-Phenylisoserines
• 1,3-dioxolan-4-one
• Mannich reaction
• benzylbenzylidenenamine

The synthesis of two new 2-phenylisoserines, each bearing a quaternary stereocenter is described. These compounds, which are analogs of the amino acid side chain found in taxol and taxotere, were obtained by addition of the lithium enolates of (2S,5S)-2-isopropyl-5-phenyl-1,3-dioxolan-4-one and (2S, 5S)-2-tert-butyl-2-methyl-5-phenyl-1,3-dioxolan-4-one to benzylbenzylideneamine in the presence of BF(3)(center dot)O(Et)(2). The diastereomeric mixtures were separated in each case and the absolute configurations thereof were determined by X-ray analysis.

• 出版日期2011