The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization

Sirilata Yotphan; Robert G. Bergman; Jonathan A. Ellman

doi:10.1021/ja710981b

The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization

Sirilata Yotphan
, Robert G. Bergman
, Jonathan A. Ellman

University of California, Berkeley

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

Bridgehead bicyclic unsaturated enamines were prepared by a tandem rhodium-catalyzed C-H bond activation/alkenylation/electrocyclization of alkyne-tethered unsaturated imines. These strained bicyclic enamines exhibit unique reactivity: for example, they give N-alkylated products upon treatment with alkylating reagents and undergo double-bond isomerization to alleviate ring strain upon reduction.

Original language	English
Pages (from-to)	2452-2453
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	8
DOIs	https://doi.org/10.1021/ja710981b
Publication status	Published - 27 Feb 2008
Externally published	Yes

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title = "The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization",

abstract = "Bridgehead bicyclic unsaturated enamines were prepared by a tandem rhodium-catalyzed C-H bond activation/alkenylation/electrocyclization of alkyne-tethered unsaturated imines. These strained bicyclic enamines exhibit unique reactivity: for example, they give N-alkylated products upon treatment with alkylating reagents and undergo double-bond isomerization to alleviate ring strain upon reduction.",

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AB - Bridgehead bicyclic unsaturated enamines were prepared by a tandem rhodium-catalyzed C-H bond activation/alkenylation/electrocyclization of alkyne-tethered unsaturated imines. These strained bicyclic enamines exhibit unique reactivity: for example, they give N-alkylated products upon treatment with alkylating reagents and undergo double-bond isomerization to alleviate ring strain upon reduction.

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The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization

Abstract

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