Cycloadditions of Alkenylboronic Derivatives

Oleksandr O. Grygorenko; Viktoriia S. Moskvina; Oleksandr V. Hryshchuk; Andriy V. Tymtsunik

doi:10.1055/s-0040-1707159

Synthesis, Table of Contents

Synthesis 2020; 52(19): 2761-2780
DOI: 10.1055/s-0040-1707159

short review

Cycloadditions of Alkenylboronic Derivatives

Oleksandr O. Grygorenko ∗

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: gregor@univ.kiev.ua

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Viktoriia S. Moskvina

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

^cV. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, Murmanska Street 1, Kyiv 02094, Ukraine

,

Oleksandr V. Hryshchuk

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: gregor@univ.kiev.ua

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Andriy V. Tymtsunik

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine Email: gregor@univ.kiev.ua

^dFaculty of Chemical Technology, National Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Peremogy Avenue 37, Kyiv 03056, Ukraine

› Author Affiliations

Abstract

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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

Keywords

organoboron compounds - cycloaddition - cyclopropanation - cyclobutanes - 1,3-dipolar cycloaddition - Diels–Alder reaction

Full Text

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