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Professor Eric Jacobsen, Harvard University

February 1, 2016 - 4:30pm
Braun Lecture Hall
S.G. Mudd Building
Stanford University

“Anion-Binding Catalysis”

About the Seminar:

Efforts spearheaded by our group and others have led to the discovery that low molecular weight, chiral organic molecules possessing distinct hydrogen-bond donor motifs catalyze an array of C–C and C–heteroatom bond-forming reactions with high enantioselectivity and broad substrate scope.  In particular, dual hydrogen bond donors such as ureas, thioureas, squaramides, and guanidinium ions have been studied in detail in the context of electrophile activation.  These catalysts operate by either of two, fundamentally different modes of electrophile activation: 1) direct hydrogen bonding to a neutral electrophile, and 2) anion binding to generate chiral ion pair.  We have applied the latter reactivity concept to several classes of cationic electrophiles that have presented long-standing challenges to asymmetric catalysis.

In this lecture, I will describe detailed kinetic and mechanistic studies of a model catalytic anion-abstraction process.  These investigations have revealed an unanticipated role of catalyst aggregation both in the ground state and in the transition state, and new strategies for the design of highly efficient catalysts.  The talk will conclude with the application of these insights to the discovery of novel glycosylation catalysts.

About the Speaker:

Eric Jacobsen was born in New York City and received his B.S. degree from New York University in 1982. His Ph.D. work was done at U.C. Berkeley under the direction of Robert Bergman. In 1986, he returned to the East Coast of the U.S. for an NIH postdoctoral fellowship at MIT with Barry Sharpless. In 1988, he began his independent career on the faculty at the University of Illinois. He moved to Harvard University as full professor in the summer of 1993, and he was named the Sheldon Emory Professor of Organic Chemistry in 2001, and he just completed an extended term as Chair of the Department of Chemistry & Chemical Biology (2010-2015).

Eric Jacobsen directs a research group dedicated to discovering useful catalytic reactions, and to applying state-of-the art mechanistic and computational techniques to the analysis of those reactions. Several of the catalysts developed in his labs have found widespread application in industry and academia. These include metal-salen complexes for asymmetric epoxidation, conjugate additions, and hydrolytic kinetic resolution of epoxides; chromium-Schiff base complexes for a wide range of enantioselective pericyclic reactions; and organic hydrogen bond-donor catalysts for activation of neutral and cationic electrophiles. Jacobsen’s mechanistic analyses of these systems have helped uncover general principles for catalyst design, including electronic tuning of selectivity, cooperative homo- and hetero-bimetallic catalysis, hydrogen-bond donor asymmetric catalysis, and anion binding catalysis.

The awards Jacobsen has received include the NSF Presidential Young Investigator Award (1990), the Packard Fellowship (1991), the Camille and Henry Dreyfus Teacher- Scholar Award (1992), the Alfred P. Sloan Foundation Fellowship (1992), the ACS Cope Scholar Award (1993), the Fluka “Reagent of the Year” Prize (1994), the Thieme-IUPAC Prize in Synthetic Organic Chemistry (1996), the Baekeland Medal (1999), the ACS Award for Creativity in Synthetic Organic Chemistry (2001), the NIH Merit Award (2002), election to the American Academy of Arts & Sciences (2004), the Mitsui Catalysis Science Award (2005), the ACS H.C. Brown Award for Synthetic Methods (2008), election to the National Academy of Sciences (2008), the Janssen Prize (2010), the Noyori Prize (2011), the Nagoya Gold Medal Prize (2011), the Chirality Medal (2012), the Remsen Award (2013), the Esselen Award (2015), and the ACS Arthur C. Cope Award (2016).

The 2015-2016 Student Hosted Colloquium is sponsored by Dow Chemical.

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