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SUMMARY:Two Short Stories: (1) Developing a versatile contrathermal Cope re
 arrangement platform for enantioselective synthesis. (2) Toward atropselec
 itve disubstitution of nitroarenes.
LOCATION:Chemistry A101
TZID:America/Denver
DTSTART:20220919T160000
UID:2026-05-03-15-16-37@natsci.colostate.edu
DTSTAMP:20260503T151637
Description:About the Seminar: \n\nTwo Short Stories: (1) Developing a ver
 satile contrathermal Cope rearrangement platform for enantioselective synt
 hesis. (2) Toward atropselecitve disubstitution of nitroarenes.\n\nThe Cop
 e Rearrangement is a classic transformation of value to organic synthesis.
  Certain substrates classes  have been well developed due to their ready 
 availability and generally favorable energetic profiles. Conversely\, 3\,3
 -dicyano-1\,5-dienes have been overlooked. We have been exploring 3\,3-dic
 yano-1\,5-dienes and have uncovered strategies to improve their energetic 
 profiles in general ways that impact their applicability to complex molecu
 le synthesis. This first half of this seminar will focus on how the marria
 ge of theory and experiment has impacted Cope rearrangement-centered strat
 egies for enantioselective synthesis.\n\nThe second portion of the talk wi
 ll focus on the development of a new strategy for achieving atropselecitve
  disubstitution of nitroarenes. The linking of carbon-based functional gro
 ups and (hetero)aromatics to (hetero)arene building blocks is critical con
 sidering the prominence of this pattern in pharmaceuticals. Modern strateg
 ies that achieve this in rapid fashion include metal-catalyzed cross-coupl
 ing\, directed C–H functionalization\, the Catellani reaction\, aryne ch
 emistry\, and many photocatalysis transformations. New methods that achiev
 e this goal and yield access to complementary\, complex (functional\, stru
 ctural\, and three-dimensional complexity) chemical space is essential to 
 the drug discovery pipeline. Disclosed at this seminar will be the the dev
 elopment of cine-ipso-disubstitution of nitroarenes: a versatile strategy 
 toward complex\, functionally-dense\, axially chiral biaryl motifs.\n\nAbo
 ut the Speaker:\n\nAlex is from the northern suburbs of Chicago. He receiv
 ed his B.A. degree from Lake Forest College under the research supervision
  of Dr. William B. Martin in 2007. He received his Ph.D. in Chemistry in 2
 012 from the University of Kansas under the guidance of Prof. Jon A. Tunge
  where he developed various decarboxylative and deacylative allylation rea
 ctions. In 2012\, he moved to Boston University to work with Prof. John A.
  Porco on complex molecule synthesis\, most notably the development of new
  routes to polyprenylatedacylphloroglucinol (PPAP) natural products and an
 alogs. Alex’s independent career began in the summer of 2014 when he joi
 ned the faculty in the Department of Chemistry at the University of Florid
 a in Gainesville. He was promoted to Associate Professor in 2021.\n\nThe G
 renning Lab’s research goals are to simplify complex molecule synthesis 
 through the invention of novel chemical methodologies and strategies and t
 o discover natural product-inspired chemotherapeutics. Some of their resea
 rch goals are supported through the NIH (R35 GM137893-01\; 2020 – 2025) 
 and the NSF (CAREER 1844443\; 2019 – 2024).\n\nOther interests include r
 ock n’ roll\, a good beer or cocktail with friends\, longboarding\, biki
 ng\, swimming\, and packin’ up the truck for a long weekend camping trip
 . 4:00 pm
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