Honors & Awards
Safety in Teaching and Research (STAR) Award, Stanford University (May 2016)
Linus Pauling Teaching Award, Stanford University (May 2015)
Camras Scholar, Illinois Institute of Technology (August 2009 to May 2013)
Professional Affiliations and Activities
Member, American Chemical Society (2010 - Present)
Education & Certifications
BS, Illinois Institute of Technology, Chemistry (2013)
Barry Trost, Doctoral Dissertation Advisor (AC)
Sulfones as Synthetic Linchpins: Transition Metal-Free sp3-sp2 and sp2-sp2 Cross-Couplings Between Geminal bis(Sulfones) and Organolithium Compounds.
Chemistry (Weinheim an der Bergstrasse, Germany)
Herein, we report a valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin. While the bis(phenylsulfonyl)methyl group is typically introduced as an sp3 carbon nucleophile, we demonstrate that it can also function as an effective sp2 carbon electrophile in the presence of organolithium nucleophiles. Akyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising a formal sp3-sp2 and sp2-sp2 cross-coupling between organolithiums and bis(sulfones). This process occurs almost instantaneously at -78 °C in the absence of any transition metals. By developing this curious transformation, we demonstrate that bis(phenylsulfonyl)methane is a valuable synthetic linchpin that can undergo two C-C bond formations as an sp3 nucleophile, followed by a third C-C bond forming reaction as an effective sp2 electrophile. This discovery significantly enhances the utility of this ubiquitous - but underutilized - linker group.
View details for DOI 10.1002/chem.201800118
View details for PubMedID 29543985
- Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous Mannich Reactions between alpha,beta- and beta,gamma-Butenolides and Aldimines JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2017; 139 (50): 18198–201
Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes
2017; 19 (9): 2346-2349
Herein, a ruthenium-catalyzed cycloisomerization that transforms 1,6-haloenynes into 5-membered carbo- and heterocycles that bear exocyclic, stereodefined, tetrasubstituted vinyl halides is reported. The reaction is insensitive to air and water, tolerates a variety of functional groups, and proceeds with good to excellent stereoselectivity and yield.
View details for DOI 10.1021/acs.orglett.7b00879
View details for Web of Science ID 000401044500038
View details for PubMedID 28436669
- The synthesis of ternary acetylides with tellurium: Li2TeC2 and Na2TeC2 RSC ADVANCES 2015; 5 (69): 55986-55993