Carbene cascades for the formation of bridged polycyclic rings

Santa Jansone-Popova; Phong Q. Le; Jeremy A. May

doi:10.1016/j.tet.2014.03.060

Carbene cascades for the formation of bridged polycyclic rings

Santa Jansone-Popova, Phong Q. Le, Jeremy A. May

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

22 Scopus citations

Abstract

A general strategy to synthesize bridged polycyclic molecules is presented. The synthesis is accomplished via a cascade reaction initiated by rhodium carbene formation. Subsequent intramolecular reaction with an alkyne is then followed by a transannular C-H bond insertion. A rationale for prediction of the major structural isomer that is formed is described and applied to a wide variety of substrates. This rationale is based on conformational and stereoelectronic considerations for the ring system in the substrate.

Original language	English
Pages (from-to)	4118-4127
Number of pages	10
Journal	Tetrahedron
Volume	70
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2014.03.060
State	Published - Jul 8 2014
Externally published	Yes

Funding

The authors are extremely grateful to Professor Huw Davies for sharing samples of the Rh 2 (S-BTPCP) 4 and Rh 2 (S-biTISP) 2 rhodium complexes. They also wish to thank the Welch Foundation for funding this research effort (Grant E-1744 ).

Funders	Funder number
Welch Foundation	E-1744

Keywords

Alkynes
Bridged rings
C-H bond insertion
Caged rings
Carbene chemistry
Cascade reactions

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10.1016/j.tet.2014.03.060

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AU - Le, Phong Q.

AU - May, Jeremy A.

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AB - A general strategy to synthesize bridged polycyclic molecules is presented. The synthesis is accomplished via a cascade reaction initiated by rhodium carbene formation. Subsequent intramolecular reaction with an alkyne is then followed by a transannular C-H bond insertion. A rationale for prediction of the major structural isomer that is formed is described and applied to a wide variety of substrates. This rationale is based on conformational and stereoelectronic considerations for the ring system in the substrate.

KW - Alkynes

KW - Bridged rings

KW - C-H bond insertion

KW - Caged rings

KW - Carbene chemistry

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JF - Tetrahedron

IS - 27-28

ER -

Carbene cascades for the formation of bridged polycyclic rings

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