2.1.4 Sigmatropic Shifts and Ene Reactions (Excluding [3,3])

A. V. Novikov; A. Zakarian

Abstract

This chapter features a review and discussion of the domino transformations initiated by ene reactions and sigmatropic rearrangements, particularly focusing on [2,3]-sigmatropic shifts, such as Mislow–Evans and Wittig rearrangements, and [1,n] hydrogen shifts. A variety of examples of these domino processes are reviewed, featuring such follow-up processes to the initial reaction as additional ene reactions or sigmatropic shifts, Diels–Alder cycloaddition, [3 + 2] cycloaddition, electrocyclization, condensation, and radical cyclization. General practical considerations and specific features in the examples of the reported cascade transformation are highlighted. To complete the discussion, uses of these cascade processes in the synthesis of natural products are discussed, demonstrating the rapid assembly of structural complexity that is characteristic of domino processes. Overall, the domino transformations initiated by ene reactions and sigmatropic shifts represent an important subset of domino processes, the study of which is highly valuable for understanding key aspects of chemical reactivity and development of efficient synthetic methods.

Key words

ene reaction - sigmatropic shift - domino reactions - cascade reactions - hydrogen shift - [1,3]-shift - [1,5]-shift - [1,7]-shift - [2,3]-shift - [3,3]-shift - Mislow–Evans rearrangement - Wittig rearrangement - Diels–Alder cycloaddition - Claisen rearrangement - oxy-Cope rearrangement - electrocyclization - chloropupukeanolide D - isocedrene - steroids - mesembrine - joubertinamine - pinnatoxins - sterpurene - arteannuin M - pseudomonic acid A

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