Ring Rearrangement of Oxo- or Aza-Bridged Bicyclo[3.2.1]octene-Based 1,5-Dienes

Evgeniya Semenova; Ouidad Lahtigui; Ion Ghiviriga; Alexander J. Grenning

doi:10.1021/acs.orglett.1c00388

Ring Rearrangement of Oxo- or Aza-Bridged Bicyclo[3.2.1]octene-Based 1,5-Dienes

Evgeniya Semenova
, Ouidad Lahtigui
, Ion Ghiviriga
, Alexander J. Grenning

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

3 Scopus citations

Abstract

We report that oxo- or aza-bridged alkylidenemalononitrile-cycloheptenes undergo a [3,3] ring rearrangement to yield cyclopenta-fused dihydro-furans or pyrroles. Described herein are the origins of the serendipitous discovery, scope studies, and representative functional group interconversion chemistry.

Original language	English (US)
Pages (from-to)	2263-2267
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.1c00388
State	Published - Mar 19 2021
Externally published	Yes

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abstract = "We report that oxo- or aza-bridged alkylidenemalononitrile-cycloheptenes undergo a [3,3] ring rearrangement to yield cyclopenta-fused dihydro-furans or pyrroles. Described herein are the origins of the serendipitous discovery, scope studies, and representative functional group interconversion chemistry.",

author = "Evgeniya Semenova and Ouidad Lahtigui and Ion Ghiviriga and Grenning, \{Alexander J.\}",

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doi = "10.1021/acs.orglett.1c00388",

language = "English (US)",

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AU - Semenova, Evgeniya

AU - Lahtigui, Ouidad

AU - Ghiviriga, Ion

AU - Grenning, Alexander J.

N1 - Publisher Copyright: ©

PY - 2021/3/19

Y1 - 2021/3/19

N2 - We report that oxo- or aza-bridged alkylidenemalononitrile-cycloheptenes undergo a [3,3] ring rearrangement to yield cyclopenta-fused dihydro-furans or pyrroles. Described herein are the origins of the serendipitous discovery, scope studies, and representative functional group interconversion chemistry.

AB - We report that oxo- or aza-bridged alkylidenemalononitrile-cycloheptenes undergo a [3,3] ring rearrangement to yield cyclopenta-fused dihydro-furans or pyrroles. Described herein are the origins of the serendipitous discovery, scope studies, and representative functional group interconversion chemistry.

UR - https://www.scopus.com/pages/publications/85103228914

UR - https://www.scopus.com/pages/publications/85103228914#tab=citedBy

U2 - 10.1021/acs.orglett.1c00388

DO - 10.1021/acs.orglett.1c00388

M3 - Article

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AN - SCOPUS:85103228914

SN - 1523-7060

VL - 23

SP - 2263

EP - 2267

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Ring Rearrangement of Oxo- or Aza-Bridged Bicyclo[3.2.1]octene-Based 1,5-Dienes

Abstract

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