Abstract

A concise method for the preparation of new 3,4,5,6-tetrahydropyrimidinium salts was presented in this paper. Further application of these salts in asymmetric diethylzinc addition of arylaldehydes was explored, giving the corresponding chiral second alcohols in good yields and moderate enantioselectivities.

Highlights

  • Since Arduengo et al reported the first isolation of stable N-heterocyclic carbene (NHCs) [1], this kind of ligand has attracted great interest, and tremendous success has been achieved in carbene chemistry [2,3,4,5,6,7,8,9,10,11,12]

  • Using commercial available amino alcohols as a starting material, we synthesized a series of enantiopure 3,4,5,6-tetrahydropyrimidinium salts (1a–1f) incorporating two hydroxyl groups and Catalysts 2018, 8, 46; doi:10.3390/catal8020046

  • Using commercial available amino alcohols as a starting material, we synthesized a series of enantiopure 3,4,5,6‐tetrahydropyrimidinium salts (1a–1f) incorporating two hydroxyl groups and Catalysts 2018, 8, x FOR PEER REVIEW

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Summary

Introduction

Since Arduengo et al reported the first isolation of stable N-heterocyclic carbene (NHCs) [1], this kind of ligand has attracted great interest, and tremendous success has been achieved in carbene chemistry [2,3,4,5,6,7,8,9,10,11,12]. Great effort has been devoted to the design and development of efficient NHC ligands in past decades. These ligands, initially considered as mimics of phosphine [13], are ubiquitous in organic chemistry because of their outstanding properties such as stronger σ-donor and weaker π-acceptor compared to the corresponding phosphane ligand, and the metal complexes of these ligands usually show better stability to moisture, air, and heat as well [14,15].

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