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

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

Key words

cyclization - diene - enyne - silaboration - triene

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