The divergent reactivity of 5-allenyloxazolidinones has been explored. This novel building block undergoes Pd(0)-catalyzed cross-coupling with boronic acids to form a wide range of chiral 1,3-dienes and pharmaceutically useful vinyloxazolidinones, the chemoselectivity being tightly controlled by a simple switch in additive.
Funding
A new molecular platform for catalytic synthesis of heterocycles
Brown, R. W., Zamani, F., Gardiner, M. G., Yu, H., Pyne, S. G. & Hyland, C. J.T. (2019). Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones. Chemical Science, 10 (39), 9051-9056.