Access to Chiral Tetrahydroquinazolines/1,3-Benzoxazines via Iridium-Catalyzed Asymmetric [4 + 2] Cycloaddition
Shengbiao Tang, Zhangru Cheng, Peng Zhang, Ying Shao, Jiangtao Sun
Abstract
An iridium-catalyzed asymmetric [4 + 2] cycloaddition of 1,3,5-triazinanes with 2-(1-hydroxyallyl)anilines/2-(1-hydroxyallyl)phenols has been developed, providing a straightforward and efficient approach to a wide range of tetrahydroquinazolines in good yields and excellent enantioselectivities (up to >99% ee). Typically, chiral 1,3-benzoxazines, which are challenging substrates in asymmetric [4 + 2] cycloaddition, could be obtained in excellent enantioselectivities via this protocol.
Topics & Concepts
CycloadditionChemistryIridiumCatalysisCombinatorial chemistryEnantioselective synthesisOrganic chemistrySynthesis of Indole DerivativesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods