Organocatalytic and metal-mediated asymmetric [3+2] cycloaddition reactions

• Published in: Coordination chemistry reviews Vol. 256; no. 11-12; pp. 938 - 952
• Main Authors: Xing, Yalan, Wang, Nai-Xing
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.06.2012
• Subjects: 1,3-Dipolar cycloaddition reactions; [3 + 2] cycloadditions; Asymmetric catalysis; Asymmetric cycloadditions; Organocatalysts; 1,3-Dipolar cycloaddition reactions; Asymmetric cycloadditions; Asymmetric catalysis; [3+2] cycloadditions; Organocatalysts
• ISSN: 0010-8545; 1873-3840
• DOI: 10.1016/j.ccr.2012.01.002

► 1,3-Dipolar reactions subject to both concerted reaction mechanism and the stepwise mechanism. ► Click chemistry is not a concerted 1,3-dipolar cycloaddition but a stepwise copper(I)-catalyzed process. ► Theoretical aspects and synthetic applications of these organocatalytic and metal-mediated asymmetric [3+2] cycloadditions are summarized. ► FMO theory to the reactivity of concerted 1,3-dipolar cycloadditions is reviewed. This review focuses on recent progress in organocatalytic and metal-mediated asymmetric [3+2] cycloadditions, including ‘click’ chemistry, asymmetric 1,3-dipolar and asymmetric non-1,3-dipolar [3+2] cycloadditions. The theoretical aspects and synthetic applications of these organocatalytic and metal-mediated asymmetric [3+2] cycloadditions are summarized. In addition, an understanding of the mechanistic details which lead to efficient stereoselectivity in organocatalytic and metal-mediated asymmetric [3+2] cycloadditions is provided. Most of the references reviewed in this paper are from 2007 upto now.