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Synthesis 2020; 52(19): 2761-2780
DOI: 10.1055/s-0040-1707159
DOI: 10.1055/s-0040-1707159
short review
Cycloadditions of Alkenylboronic Derivatives
The work was funded by Enamine Ldt. and Ministry of Education and Science of Ukraine (Grant No. 19BF037-03).Further Information
Publication History
Received: 25 March 2020
Accepted after revision: 22 May 2020
Publication Date:
24 June 2020 (online)
Abstract
The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.
1 Introduction
2 [2+1] Cycloaddition
2.1 Cyclopropanation
2.1.1 With Methylene Synthetic Equivalents
2.1.2 With Substituted Carbenoids
2.2 Epoxidation
2.3 Aziridination
3 [2+2] Cycloaddition
4 [3+2] Cycloaddition
4.1 With Nitrile Oxides
4.2 With Diazoalkanes
4.3 With Nitrones
4.4 With Azomethine Ylides
5 [4+2] Cycloaddition
6 [4+3] Cycloaddition
7 Conclusions and Outlook
-
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