Synthesis 2022; 54(13): 2927-2975
DOI: 10.1055/a-1771-0641
review

Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

Regina Westphal
a   Chemistry Department, Espírito Santo Federal University, Avenida Fernando Ferrari 514, Goiabeiras, Vitória, ES, Brazil
,
Eclair Venturini Filho
a   Chemistry Department, Espírito Santo Federal University, Avenida Fernando Ferrari 514, Goiabeiras, Vitória, ES, Brazil
,
Fabrizio Medici
b   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19 Milano, Italy
,
b   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19 Milano, Italy
,
Sandro J. Greco
a   Chemistry Department, Espírito Santo Federal University, Avenida Fernando Ferrari 514, Goiabeiras, Vitória, ES, Brazil
› Author Affiliations
M.B. thanks Ministero dell’Istruzione, dell’Università e della Ricerca (MUR) for the project PRIN 2017 NATURECHEM. F.M. also thanks MUR project PRIN 2017 NATURECHEM for a postdoctoral fellowship. S.J.G. thanks Conselho Nacional de Desenvolvimento Científico e Tecnológico for financial support.


Abstract

This review summarizes the latest developments in asymmetric domino reactions, with the emphasis on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, the reaction mechanisms, the rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included when appropriate.

1 Introduction

2 Asymmetric Domino Reactions

2.1 Domino Reactions Initiated by Michael Reactions

2.2 Domino Reactions Initiated by Mannich Reactions

2.3 Domino Reactions Initiated by Knoevenagel Reactions

2.4 Domino Reactions Initiated by Cycloaddition Reactions

2.5 Domino Reactions Initiated by Metal Insertion

2.6 Other Mechanisms

3 Conclusion



Publication History

Received: 20 December 2021

Accepted after revision: 14 February 2022

Accepted Manuscript online:
14 February 2022

Article published online:
16 May 2022

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