Enantioselective [3 + 2] cycloadditions of terminal allenoates with β-sulfonyl-α,β-unsaturated ketones
Xiuzheng Li, Liao Jun, Xiaobin Zhuo, Huamin Wang, Xiaoyun Chai, Yan Zou, Qingjie Zhao
Abstract
A highly efficient and mild method for [3 + 2] cycloaddition of β-sulfonyl-α,β-unsaturated ketones with terminal allenoates was well-explored and developed. The reactions were successfully performed by applying multifunctional chiral phosphine P6 which was screened from eight chiral phosphorus reagents to finally result in a variety of enantioenriched sulfone-substituted cyclopentenes with two chiral centers (up to 81% yield with 94% ee). Moreover, 2.5 mol% catalytic equivalents were proved to be feasible when this reaction was performed on a 10 mmol scale.
Topics & Concepts
Enantioselective synthesisSulfonylCycloadditionSulfonePhosphineYield (engineering)ReagentChemistryCatalysisOrganic chemistryCombinatorial chemistryMedicinal chemistryMaterials scienceAlkylMetallurgySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods