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[3,3] Ring Rearrangement of Oxo- or Aza-Bridged Bicyclo[3.2.1]octene-Based 1,5-Dienes

https://doi.org/10.1021/acs.orglett.1c00388

Semenova, Evgeniya; Lahtigui, Ouidad; Ghiviriga, Ion; Grenning, Alexander J. (March 2021, Organic Letters)
null (Ed.)
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Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements

https://doi.org/10.1021/acs.joc.0c02690

Fereyduni, Ehsan; Lahtigui, Ouidad; Sanders, Jacob N.; Tomiczek, Breanna M.; Mannchen, Michael D.; Yu, Roland A.; Houk, K. N.; Grenning, Alexander J. (February 2021, The Journal of Organic Chemistry)
null (Ed.)
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Selective ring-rearrangement or ring-closing metathesis of bicyclo[3.2.1]octenes

https://doi.org/10.1039/d0cc04624h

Semenova, Evgeniya; Lahtigui, Ouidad; Scott, Sarah K.; Albritton, Matthew; Abboud, Khalil A.; Ghiviriga, Ion; Roitberg, Adrian E.; Grenning, Alexander J. (October 2020, Chemical Communications)
null (Ed.)
Explored was the competitive ring-closing metathesis vs. ring-rearrangement metathesis of bicyclo[3.2.1]octenes prepared by a simple and convergent synthesis from bicyclic alkylidenemalono-nitriles and allylic electrophiles. It was uncovered that ring-closing metathesis occurs exclusively on the tetraene-variant, yielding unique, stereochemically and functionally rich polycyclic bridged frameworks, whereas the reduced version (a triene) undergoes ring-rearrangement metathesis to 5 – 6 – 5 fused ring systems resembling the isoryanodane core.
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