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Chemistry Guest Seminars

Organic Seminars 2020

Thursday, January 30, 1:00-2:00, NHB 1.720biscoe

Rethinking asymmetric synthesis: the development of enantiospecific Pd-catalyzed cross-coupling reactions

Mark Biscoe

Associate Professor

City College of New York

Biscoe Group

ABSTRACT: The development of transition metal-catalyzed cross-coupling reactions has greatly influenced the manner in which the synthesis of complex organic molecules is approached. A wide variety of methods are now available for the formation of C(sp2)–C(sp2) bonds, and more recent work has focused on the use of C(sp3) electrophiles and nucleophiles. However, the use of secondary alkyl nucleophiles in cross-coupling reactions remains an outstanding challenge because of slow alkyl transmetallation and the tendency of alkyl groups to isomerize under the reaction conditions. In principle, cross-coupling reactions that employ enantioenriched secondary alkyl nucleophiles can proceed in an enantiospecific manner where the original stereochemistry is transferred to the coupling product.  This constitutes a novel approach to the preparation of enantioenriched molecules in which stereochemistry is introduced prior to direct reaction at a stereocenter.  In this seminar, we will describe new methods for the use of configurationally stable, optically active alkyltin and alkylboron nucleophiles in enantiospecific Pd-catalyzed cross-coupling reactions. Such processes enable the rapid generation of libraries of non-racemic drug candidates from a single optically active precursor.


Publications (Group Site)

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h-index: 16  Total Articles: 23  Total Citations:  1730 (Web of Science, Jan. 2020)

Tuesday, January 21, 2:00-3:00, NHB 1.720narayan

Biocatalysis and complex molecule synthesis

Alison Narayan

Assistant Professor

University of Michigan

Narayan Lab

Abstract:  Natural sources, such as plants, fungi and microbes, have historically provided compounds with potent pharmaceutical properties. While it can be challenging to build complex natural products in a lab using existing chemistry methods, Nature has perfected these biosynthetic pathways. The work described leverages the power of Nature’s tools for building complex molecules to synthesize novel molecules with therapeutic potential.  The reactivity and selectivity of enzymes from natural product pathways are often unparalleled in existing chemical methods. Enzymes with potential synthetic utility are used as a starting point for engineering biocatalysts with (1) broad substrate scope, (2) high catalytic efficiency, and (3) exquisite site- and stereoselectivity. These biocatalytic methods are employed to efficiently synthesize biologically active complex molecules.


Publications (Group Site)

Publications (Google Scholar Citations)

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h-index: 11  Total Articles: 21  Total Citations:  508 (Web of Science, Dec. 2019)

h-index: 15  Total Citations: 1055 (Google Scholar Citations, Dec. 2019)

Faculty Recruiting Seminar

Monday, January 13, 3:30pm - 4:30pm, WEL 2.122yang

Innovation in Asymmetric Catalysis by Bridging Chemistry and Biology

Yang Yang

Caltech

Postdoctoral Researcher - NIH Ruth L. Kirschstein NRSA Postdoctoral Fellowship

PhD MIT, 2017 (Buchwald)

Frances Arnold Group

We repurpose diverse existing proteins and their promiscuous functions for new chemistries, generate catalysts for ncAA formation, and design new ML-based approaches for directed evolution.


Publicatons (Google Scholar Citations)

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h-index: 21  Total Citations: 1533  (Google Scholar Citations, Dec. 2019)

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