Enantioselective Allylation of Cyclic and In Situ Formed N-Unsubstituted Imines with Tetraol-Protected Allylboronates

Tetraol-protected alpha-chiral allylboronates are utilized in diastereo- and enantioselective transformations of cyclic imines (up to 98 %, d.r. 97 : 3, e.r. 99 : 1). An application to in situ formed N-unsubstituted imines gives in a consecutive one-pot sequence selective access to all four stereoisomers of the homoallylamine within minutes (up to 88 %, d.r. 81 : 19, e.r. 99 : 1). These results underline the usability, tuneability and stability of tetraol-based allylboronates.

Automated summary

In this study, tetraol-protected alpha-chiral allylboronates were used for the diastereo- and enantioselective transformations of cyclic imines, showing high efficiency and stability. The consecutive one-pot sequence for in situ formed N-unsubstituted imines provided selective access to all four stereoisomers of homoallylamine in minutes, demonstrating the utility and tunability of tetraol-based allylboronates.