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Synthesis 2012(4): 504-512  
DOI: 10.1055/s-0031-1289681
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Enantioselective Alkylations with Allylic Alcohols

Marco Bandini*, Gianpiero Cera, Michel Chiarucci
Dipartimento di Chimica ‘G. Ciamician’, Alma Mater Studiorum, Università di Bologna, via Selmi 2, 40126 Bologna, Italy
Fax: +39(51)2099456; e-Mail: marco.bandini@unibo.it;
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Publication History

Received 23 November 2011
Publication Date:
26 January 2012 (online)

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Abstract

Allylic alcohols have recently risen to prominence as a valuable synthetic alternative to classic activated alkylating agents in asymmetric catalysis. The intrinsic drawbacks that limited their employment in catalytic enantioselective transformations, until recently, have been efficiently addressed providing elegant solutions. This short review intends to summarize the most salient and recent outcomes in this emerging research area, highlighting the scope and limitations of the most selective catalytic methodologies.

1 Introduction

2 Redox Metal Catalysis

2.1 C-C Bond-Forming Reactions

2.2 C-N and C-O Bond-Forming Reactions

3 Electrophilic Activation of C=C

3.1 C-C Bond-Forming Reactions

3.2 C-N and C-O Bond-Forming Reactions

4 Substitution via Carbocation Intermediates

5 Conclusions

Key words

alkylation reactions - allylic alcohols - asymmetric synthesis - enantioselection - metal/organocatalysis

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