Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C-H bond insertion

Santa Jansone-Popova; Jeremy A. May

doi:10.1021/ja308305z

Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C-H bond insertion

Santa Jansone-Popova
, Jeremy A. May

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

79 Scopus citations

Abstract

A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C-H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.

Original language	English
Pages (from-to)	17877-17880
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	43
DOIs	https://doi.org/10.1021/ja308305z
State	Published - Oct 31 2012
Externally published	Yes

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title = "Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C-H bond insertion",

abstract = "A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C-H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.",

author = "Santa Jansone-Popova and May, \{Jeremy A.\}",

year = "2012",

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day = "31",

doi = "10.1021/ja308305z",

language = "English",

volume = "134",

pages = "17877--17880",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

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T1 - Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C-H bond insertion

AU - Jansone-Popova, Santa

AU - May, Jeremy A.

PY - 2012/10/31

Y1 - 2012/10/31

N2 - A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C-H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.

AB - A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C-H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.

UR - https://www.scopus.com/pages/publications/84868093881

U2 - 10.1021/ja308305z

DO - 10.1021/ja308305z

M3 - Article

C2 - 23083300

AN - SCOPUS:84868093881

SN - 0002-7863

VL - 134

SP - 17877

EP - 17880

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 43

ER -

Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C-H bond insertion

Abstract

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