Synthesis 2020; 52(19): 2761-2780
DOI: 10.1055/s-0040-1707159
short review
© Georg Thieme Verlag Stuttgart · New York

Cycloadditions of Alkenylboronic Derivatives

a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: [email protected]
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
Viktoriia S. Moskvina
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
c  V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, Murmanska Street 1, Kyiv 02094, Ukraine
,
Oleksandr V. Hryshchuk
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: [email protected]
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
Andriy V. Tymtsunik
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   Email: [email protected]
d  Faculty of Chemical Technology, National Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Peremogy Avenue 37, Kyiv 03056, Ukraine
› Author Affiliations
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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