Selected Synthetic Strategies
to Spirocyclics

Sambasivarao Kotha; Ashoke Chandra Deb; Kakali Lahiri; Ethirajan Manivannan

doi:10.1055/s-0028-1083300

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Synthesis 2009(2): 165-193
DOI: 10.1055/s-0028-1083300

REVIEW

Selected Synthetic Strategies to Spirocyclics

Sambasivarao Kotha*, Ashoke Chandra Deb, Kakali Lahiri, Ethirajan Manivannan
Department of Chemistry, Indian Institute of Technology-Bombay, Mumbai 400076, India
Fax: +91(22)25723480; e-Mail: srk@chem.iitb.ac.in;

Further Information

Publication History

Received 19 September 2008
Publication Date:
09 January 2009 (online)

Abstract
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Abstract

The design and synthesis of spirocycles is a challenging task because it involves the creation of a quaternary center, which itself is considered to be one of the most difficult tasks among synthetic transformations. Some recent approaches based on metathesis, cycloaddition and transition-metal-mediated transformations to spirocycles are described here.

1 Introduction

2 Scope of the Review

3 Alkylation Methods

4 Transition-Metal-Based Approaches

5 Rearrangement-Based Approaches

6 Ring-Expansion Method

7 Ring-Contraction Method

8 Photochemical Approaches

9 Ring Closure of Geminally Disubstituted Compounds

10 Cycloaddition Tactics

11 Other Cyclization Methods

12 Metathesis Approaches

13 Pauson-Khand Reaction

14 Conclusions and Future Prospects

Key words

spiro compounds - metathesis - Diels-Alder reactions - domino reactions - Suzuki coupling - radical reactions - ring closure

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