Synthesis 2020; 52(21): 3129-3139
DOI: 10.1055/s-0040-1707247
short review
© Georg Thieme Verlag Stuttgart · New York

Silylboranes as Powerful Tools in Organic Synthesis: Stereo- and Regioselective Reactions with 1,n-Enynes

Department of Chemistry, Organic Chemistry, KTH Royal Institute of Technology, 10044 Stockholm, Sweden   Email: [email protected]
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Further Information

Publication History

Received: 08 June 2020

Accepted after revision: 13 July 2020

Publication Date:
20 August 2020 (online)


Abstract

Bismetalated alkenes, accessible by element–element addition to alkynes, are valuable building blocks in organic synthesis, providing wide opportunities for divergent synthesis. Silaboration of alkynes with a pendant olefinic group, catalyzed by group 10 metal complexes, and subsequent transformation of the silicon and boron functional groups give access to densely functionalized 1,3-dienes and 1,3,5-trienes with defined stereo- and regiochemistry, 1,2-dienes, and carbocyclic and heterocyclic products.

1 Introduction

2 Background

3 Reactions with 1,3-Enynes

4 Cyclization 1,6-Enynes

5 Cyclization 1,7-Enynes

6 Cyclization of 1,n-Enynes (n > 7)

7 Cyclization of Dienynes and Enediynes

8 Cyclization of 1,6-Diynes

9 Conclusions

 
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