Synthesis 2021; 53(13): 2167-2182
DOI: 10.1055/a-1389-1438
short review

1,3-Bifunctional Nucleophilic Allylation Reagents: Preparative Methods and Synthetic Applications

Jiaming Liu
,
Ming Chen
Financial support provided by Auburn University is gratefully acknowledged.


Abstract

1,3-Bifunctional nucleophilic allylation reagents play an important role in organic synthesis. In this short review, we summarize the methods for the preparation of 1,3-bifunctional reagents and their reactions with various electrophiles. Synthetic applications of these reagents in the context of complex molecule synthesis are also discussed.

1 Introduction

2 Reagent Synthesis

2.1 Symmetrical Reagents

2.2 Unsymmetrical Reagents

2.2.1 Bis-silane and Silyl-stannane Reagents

2.2.2 Bis-boron and Silyl-boron Reagents

3 Synthetic Applications

3.1 Allylation of Aldehydes

3.2 Allylation of Ketones

3.3 Allylation of Imines

3.4 Allylation of Other Electrophiles with 1,3-Bifunctional Allylation Reagents

4 Summary



Publication History

Received: 24 December 2020

Accepted after revision: 11 February 2021

Publication Date:
11 February 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
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