C_(2)轴手性双胍催化叶立德和不饱和吖内酯的串联反应研究

Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C_(2)-axis Chiral Biguanide

本文成功合成了4种基于联二萘酚骨架的手性双胍-酰胺类催化剂,并将其应用于邻羟基苯甲醛亚甲胺叶立德与不饱和吖内酯的1,3-偶极环加成和分子内串联反应。研究表明,在室温下以CHCl_(3)作为溶剂、轴手性胍(1b,10(mol)%)作为催化剂,反应12h,能以较好的收率(73%~88%)和较高的对映选择性(72%~86%)得到苯并吡喃衍生物。

In this paper,four chiral biguanide-amide catalysts based on the BINOL framework were successfully synthesized and applied to the 1,3-dipolar cycloaddition and intramolecular tandem reaction of o-hydroxybenzaldehyde ylide and unsaturated azlactone.Using CHCl3 as the solvent and axial chiral guanidine(1 b,10(mol)%)as the catalyst,reacting at room temperature for 12 hours,a series of benzopyran derivatives can be obtained with good yield(73%~88%)and high enantioselectivity(72%~86%).