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

Jiaming Liu; Ming Chen

doi:10.1055/a-1389-1438

Synthesis, Table of Contents

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∗

Abstract

All articles of this category

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

Key words

1,3-bifunctional allylation reagents - C–C bond formation - natural products - enantioselective - stereoselective synthesis

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References

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82 As coined by Hall, the 1,3-bifunctional allylation reagents that we surveyed in this short review belong to type II double allylation reagents; see: Peng, F.; Hall, D. G. J. Am. Chem. Soc. 2007, 129, 3070. Another class of 1,3-bifunctional allylation reagents are the type I double allylation reagents. Such reagents react with a first electrophile E1 and simultaneously reveal a second allylic metal unit that can react with another electrophile E2. Due to space limitations of the present review, such reagents (type I) will be the topic of a future review