Assessing the halogen effect in Diels-Alder reactions involving chiral alpha-halo enones. A combined experimental and DFT computational approach

作者：Sarotti Ariel M; Spanevello Rolando A; Suarez Alejandra G^*

来源：Tetrahedron Letters, 2011, 52(32): 4145-4148.

DOI：10.1016/j.tetlet.2011.05.143

• Levoglucosenone
• alpha-Halo enone
• Diels-Alder
• Reactivity
• DFT

An experimental and computational study was conducted to assess the effect of chlorine and bromine substitution in Diels-Alder reactions involving chiral alpha-halo enones as dienophiles. An important rate enhancement was observed in the case of acyclic dienes, while the use of cyclic dienes resulted in prolonged reaction times and lower yields. DFT calculations suggest that these reactions are governed by finely balanced geometric and electronic features at the TSs.

• 出版日期2011-8-10