Stereochemistry of Phosphite Addition to Azomethine Bond of Achiral 2,6-Pyridinedicarbaldimines and Isophthalaldimines—A Comparative Study

Abstract

The addition of dialkyl H-phosphonates to isophthalaldimines 1a–d and pyridine-2,6-dicarboxaldimines 2a–d was investigated and led to the corresponding aminophosphonates. Diastereoselectivity of the addition to pyridine-2,6-dicarboxaldimines was lower than to isophthalaldimines. In contrast, addition of bis(trimethylsilyl) H-phosphonate to both groups of aldimines demonstrated that the diastereoselectivity in case of pyridine-2,6-dicarboxaldimines is comparable or even better than that for the isophthalic derivatives.

GRAPHICAL ABSTRACT

Keywords:

• Addition
• azomethine bond
• dialkyl H-phosphonates
• diastereoselectivity
• isophthalaldimines
• pyridine-2,6-dicarboxaldimines

Acknowledgments

Marek Dzięgielewski was the participant of the project entitled Doktoranci—Regionalna Inwestycja w Młodych naukowców—Akronim D-RIM, which is co-financed by the EU from the European Social Fund in the framework of the Operational Programme Human Capital, Priority VIII, Subaction 8.2.1. and is thankful for the scholarship.