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Diastereoselective [3 + 2] Cycloaddition of Lewis Acidic Alkenylboranes and Aldehydes
Fei Liu1, Tongdao Wang1,2
1School of Chemistry, Dalian University of Technology, Dalian 116024, P. R. China.
None:
The [3 + 2] cycloaddition of Lewis acidic alkenylboranes with aldehydes is described, providing a high-yielding and stereoselective approach for the synthesis of five-membered boron-containing heterocycles. Notably, alkenylboranes are used as three-atom B-C═C building blocks. The reaction proceeded smoothly under mild conditions and formed three contiguous stereogenic centers. Additionally, the reaction tolerated a wide variety of substituents on aldehydes and led to BOC3 cyclic scaffolds in 71-98% isolated yields and up to 20:1 dr.
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