Organocatalytic and metal-mediated asymmetric [3+2] cycloaddition reactions
► 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 asy...
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| Published in | Coordination chemistry reviews Vol. 256; no. 11-12; pp. 938 - 952 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier B.V
01.06.2012
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| Abstract | ► 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. |
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| AbstractList | ► 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. |
| Author | Xing, Yalan Wang, Nai-Xing |
| Author_xml | – sequence: 1 givenname: Yalan surname: Xing fullname: Xing, Yalan organization: Department of Chemistry & Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA – sequence: 2 givenname: Nai-Xing surname: Wang fullname: Wang, Nai-Xing email: nxwang@mail.ipc.ac.cn organization: Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China |
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| Keywords | 1,3-Dipolar cycloaddition reactions Asymmetric cycloadditions Asymmetric catalysis [3+2] cycloadditions Organocatalysts |
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| Snippet | ► 1,3-Dipolar reactions subject to both concerted reaction mechanism and the stepwise mechanism. ► Click chemistry is not a concerted 1,3-dipolar cycloaddition... |
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| SubjectTerms | 1,3-Dipolar cycloaddition reactions [3 + 2] cycloadditions Asymmetric catalysis Asymmetric cycloadditions Organocatalysts |
| Title | Organocatalytic and metal-mediated asymmetric [3+2] cycloaddition reactions |
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