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Gold- and Platinum-Catalyzed Reactions of Enynes Read chapter Read first chapter

2014 | OriginalPaper | Chapter

2. New Advances in the Gold-Catalyzed Cycloisomerization Reactions of Enynes: 1,5-hydride Shifts and Access to Ketomacrolactones

Author : Antoine Simonneau

Published in: Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes

Publisher: Springer International Publishing

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Excerpt

In this chapter will be presented some new results obtained in the field of gold catalyzed cycloisomerizations of 1,6-enynes. A new reaction based on a 1,5-hydride shift process has been disclosed, allowing the formation of functionalized allenes. The end of this chapter gathers some results we got toward the synthesis of macrocyles using a gold catalyzed cycloisomerization reaction of oxygen-tethered 1,6-enynes. Before the results being described and discussed, we will briefly introduce other gold catalyzed reactions that feature 1,5-hydride shifts. …

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previous chapter Gold- and Platinum-Catalyzed Reactions of Enynes
next chapter Synthesis of Polyconjugated Bis-Enones Through a Gold-Catalyzed 1,3-Acyloxy Migration-Cyclization-1,5-Acyl Shift Cascade Reaction
Footnotes
1
For a selection of recent reviews on C-H bond functionalization, see: [1‐4]. See also [5].
 
2
For a review gathering some examples of this type of reaction see: [9].
 
3
With Pt(IV): [10].
 
4
With cationic Au(I): [11].
 
5
Sames also invoked the possibility of a platinum vinylidene, see Ref. [10].
 
6
See also Ref. [21].
 
7
However, as discussed in Chap.​ 1, Sect. 1.5.1, formation of 53 can also arise from a 1,2-OAc shift/cyclopropanation sequence, but it was not evoked by the authors.
 
8
See also: [37 ].
 
9
For a study where prenyl double bonds showed distinct behaviors, see Ref. [38 ].
 
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Metadata
Title
New Advances in the Gold-Catalyzed Cycloisomerization Reactions of Enynes: 1,5-hydride Shifts and Access to Ketomacrolactones
Author
Antoine Simonneau
Copyright Year
2014
Book
Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes

Print ISBN: 978-3-319-06706-3

Electronic ISBN: 978-3-319-06707-0

Copyright Year: 2014

DOI
https://doi.org/10.1007/978-3-319-06707-0_2

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