Functional Group Scope in the Methylene-Free, Tandem Enyne Metathesis

Peppers, Brian P.; Kulkarni, and Amol A.; Diver, Steven T.

doi:10.1021/ol060727d

Cited by 27 publications

(8 citation statements)

References 11 publications

(19 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tandem metathesis between alkynes and dienes provides an useful and efficient way for ring synthesis. Diver and co‐workers recently reported the synthesis of cyclohexadienes via tandem metathesis starting from different alkynes and using cyclooctadiene 17. We reasoned that tandem metathesis could be a shorter and elegant approach for the synthesis of enantiopure benzhydrylamines starting from bromo‐propargylamide ( R )‐ 1f which was not reported in our previous work 8.…”

Section: Resultsmentioning

confidence: 82%

Practical Syntheses of Enantiomerically Pure N‐Acetylbenzhydrylamines

et al. 2007

View full text Add to dashboard Cite

Two practical routes for the synthesis of benzhydrylamine derivatives in enantiomerically pure form have been developed. N-Acetylbenzhydrylamines can be synthesised in few steps and good yields starting from 1-aryl-1-propargylamines. The key steps are represented by the alkenealkyne cross metathesis reaction and alkyne-diene methylene-free tandem-metathesis reaction; these reactions have been performed under microwave irradiation in a few min-

show abstract

Section: Resultsmentioning

confidence: 82%

Practical Syntheses of Enantiomerically Pure N‐Acetylbenzhydrylamines

et al. 2007

View full text Add to dashboard Cite

show abstract

“…In more difficult cases, such as those employing coordinating heteroatoms on the alkyne or internal alkynes, higher concentrations of 1,5-cyclooctadiene or the polymer polybutadiene are needed. 139 Some representative products are illustrated in Table 19.…”

Section: Ring Synthesismentioning

confidence: 99%

5.27 Ene–Yne Metathesis

Diver

Clark

2014

Comprehensive Organic Synthesis II

View full text Add to dashboard Cite

“…[85] The chiral α-amino ester 110 underwent tandem metathesis with excess COD in high NMR yield and with excellent isolated yield (eq 62). This substrate has a free NH proton and previously could be synthesized in only 36% yield with difficulty in the isolation.…”

Section: Vinyl Carbene Equilibration: Methylene-free Enyne Metathesismentioning

confidence: 99%

Ruthenium vinyl carbene intermediates in enyne metathesis

Diver

2007

Coordination Chemistry Reviews

Self Cite

View full text Add to dashboard Cite

This review provides an overview of ruthenium vinyl carbene reactivity as it relates to enyne metathesis. Methods for the synthesis of metathesis-active and metathesis-inactive complexes are also summarized. Some of the early hypotheses about vinyl carbene intermediates in enyne metatheses were tested in the arena of synthetic chemistry and subsequently led to mechanistic studies. In these two areas, studies from the author's labs are described. There are still many unresolved questions in enyne metathesis that trace back to vinyl carbene reactivity. Hopefully this review will stimulate further investigation into vinyl carbene reactivity which should further refine our understanding of catalytic enyne metathesis.

show abstract

Functional Group Scope in the Methylene-Free, Tandem Enyne Metathesis

Abstract: The methylene-free ring synthesis of 1,3-cyclohexadienes has been expanded to include a diverse set of functional group-rich terminal and internal alkynes. [reaction: see text]

Cited by 27 publications

References 11 publications

Practical Syntheses of Enantiomerically Pure N‐Acetylbenzhydrylamines

Practical Syntheses of Enantiomerically Pure N‐Acetylbenzhydrylamines

5.27 Ene–Yne Metathesis

Ruthenium vinyl carbene intermediates in enyne metathesis

Contact Info

Product

Resources

About