Journal
CHEMICAL SCIENCE
Volume 13, Issue 7, Pages 1951-1956Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc06307c
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Funding
- NIH NIGMS [R35 GM137893-01]
- National Science Foundation [NSF CAREER 1844443]
- ACS Division of Organic Chemistry
- NIH [S10 OD021758-01A1]
- University of Florida - Research Computing
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A strategy for constructing vicinal 4 degrees/3 degrees carbons via reductive Cope rearrangement is reported herein. Substrates with Cope rearrangement kinetic barriers of approximately 23 kcal mol(-1) and isoenergetic favorability (Delta G approximately 0) have been designed. These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction into useful polyfunctionalized building blocks.
Herein reported is a strategy for constructing vicinal 4 degrees/3 degrees carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of similar to 23 kcal mol(-1) with isoenergetic favorability (Delta G similar to 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.
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