Construction of bridged and fused ring systems via intramolecular michael reactions of vinylnitroso compounds

Ilia Korboukh; Praveen Kumar; Steven M. Weinreb

doi:10.1021/ja074108r

Construction of bridged and fused ring systems via intramolecular michael reactions of vinylnitroso compounds

Ilia Korboukh
, Praveen Kumar
, Steven M. Weinreb

Chemistry

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

37 Scopus citations

Abstract

The first examples of intramolecular Michael-type reactions of in situ-formed vinylnitroso compounds with carbon nucleophiles are reported. This methodology has been used to prepare a variety of ring systems including [3.2.1]-, [2.2.2]-, and [2.2.1]-bridged carbobicyclic compounds, as well as a fused [5.5]-ring compound. Malonate anions have proven to be effective carbon nucleophiles in these conjugate addition reactions, and simple ester potassium enolates have also been successfully employed.

Original language	English (US)
Pages (from-to)	10342-10343
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	34
DOIs	https://doi.org/10.1021/ja074108r
State	Published - Aug 29 2007

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja074108r

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abstract = "The first examples of intramolecular Michael-type reactions of in situ-formed vinylnitroso compounds with carbon nucleophiles are reported. This methodology has been used to prepare a variety of ring systems including [3.2.1]-, [2.2.2]-, and [2.2.1]-bridged carbobicyclic compounds, as well as a fused [5.5]-ring compound. Malonate anions have proven to be effective carbon nucleophiles in these conjugate addition reactions, and simple ester potassium enolates have also been successfully employed.",

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AU - Kumar, Praveen

AU - Weinreb, Steven M.

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Y1 - 2007/8/29

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AB - The first examples of intramolecular Michael-type reactions of in situ-formed vinylnitroso compounds with carbon nucleophiles are reported. This methodology has been used to prepare a variety of ring systems including [3.2.1]-, [2.2.2]-, and [2.2.1]-bridged carbobicyclic compounds, as well as a fused [5.5]-ring compound. Malonate anions have proven to be effective carbon nucleophiles in these conjugate addition reactions, and simple ester potassium enolates have also been successfully employed.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 34

ER -

Construction of bridged and fused ring systems via intramolecular michael reactions of vinylnitroso compounds

Abstract

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