Garratt–Braverman Cyclization, a Powerful Tool for C–C Bond Formation

Sayantan Mondal; Tapobrata Mitra; Raja Mukherjee; Partha Sarathi Addy; Amit Basak

doi:10.1055/s-0032-1317321

Synlett, Table of Contents

Synlett 2012; 23(18): 2582-2602
DOI: 10.1055/s-0032-1317321

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Garratt–Braverman Cyclization, a Powerful Tool for C–C Bond Formation

Sayantan Mondal

Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India Fax: +91(3222)282252 Email: absk@chem.iitkgp.ernet.in

,

Tapobrata Mitra

Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India Fax: +91(3222)282252 Email: absk@chem.iitkgp.ernet.in

,

Raja Mukherjee

Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India Fax: +91(3222)282252 Email: absk@chem.iitkgp.ernet.in

,

Partha Sarathi Addy

Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India Fax: +91(3222)282252 Email: absk@chem.iitkgp.ernet.in

,

Amit Basak*

Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India Fax: +91(3222)282252 Email: absk@chem.iitkgp.ernet.in

› Author Affiliations

Abstract

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Abstract

Development of new strategies for C–C bond formation remains in the forefront of organic synthesis. The base-mediated rearrangement of bis-propargyl sulfones via bis-allenes generated in situ, now known as the Garratt–Braverman cyclization (GBC), leads to the formation of two new C–C bonds. The reaction has recently drawn attention from organic chemists due to the wide scope as well as interesting mechanism. This report aims to give an account of the developments in this area with particular emphasis on synthetic applications.

1 Introduction

2 Biradical-Generating Reactions

3 Fate of Biradicals

4 Garratt–Braverman Cyclization; A Historical Development

5 Exploration of Garratt–Braverman Chemistry in Organic Synthesis

5.1 Braverman’s Work

5.2 Feldman’s Work

5.3 Contribution from the Author’s Group

6 Competition between GBC and Biradical/Concerted Cyclization Reactions

6.1 GBC vs. MSC/SC

6.2 GBC vs. 6π-Electrocyclization

6.3 GBC vs. Nucleophilic Addition

7 Conclusion and Future Aspects

Key words

alkynes - cyclizations - ene reactions - polyclyclic compounds - radicals - sulfones

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References

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