Masayuki Wasa

Masayuki Wasa,

ASO PROF

Department: SR-CHEM-WASA LAB
Business Phone: (561) 228-2476
Business Email: wasam@ufl.edu

About Masayuki Wasa

Research Profile

Preparation of various organic compounds of synthetic, biological, and medicinal significance in a cost-effective, efficient, reliable and selective manner is vital to advances in human health care. The central theme of the Wasa research program is the development of synthetic methods that possess these desirable attributes and allow rapid access to the important molecules from an array of readily accessible but otherwise chemically inert starting materials.

Synthesis of a target molecule can often be accelerated through the use of a catalyst system; the catalysts facilitate the union of poorly reactive starting materials by converting them into a set of highly reactive intermediates en route to the products. Nonetheless, key shortcomings limit the application of catalytic methods in complex molecule synthesis. Among the critical unresolved issues in the state-of-the-art is the catalyst deactivation, occurring through the formation of stable adducts within a reaction mixture of the catalysts, starting materials, intermediates and/or products. Such process can either result in deceleration or termination of the target reaction. To suppress catalyst deactivation, the range of starting materials is confined to those that pose minimum risk of generating the inert adducts.

The aim of our research team is to address these problems through the design and development of highly efficient and multi-functional catalyst systems that cannot be easily disabled/quenched. We aspire to demonstrate that our catalysts may be used for direct conversion of complex natural products, pharmaceuticals, and agrochemicals to a variety of derivatives of interest.

Publications

Academic Articles
2023
Chemical Tagging of Bioactive Amides by Cooperative Catalysis: Applications in the Syntheses of Drug Conjugates
Journal of the American Chemical Society. 145(26):14233-14250 [DOI] 10.1021/jacs.3c00169. [PMID] 37341172.
2022
Enantioselective Organocopper-Catalyzed Hetero Diels-Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers.
Journal of the American Chemical Society. 144(14):6173-6179 [DOI] 10.1021/jacs.2c01656. [PMID] 35380438.
2021
Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3 and a Chiral Lewis Acid Co-Catalyst.
Journal of the American Chemical Society. 143(5):2441-2455 [DOI] 10.1021/jacs.0c13200. [PMID] 33512998.
2020
B(C6F5)3-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D2O.
Advanced synthesis & catalysis. 362(2):360-364 [DOI] 10.1002/adsc.201901419. [PMID] 32256276.
2020
Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.
Journal of the American Chemical Society. 142(38):16493-16505 [DOI] 10.1021/jacs.0c08599. [PMID] 32830966.
2020
Sequential Conia-ene-type cyclization and Negishi coupling by cooperative functions of B(C6F5)3, ZnI2, Pd(PPh3)4 and an amine.
Organic & biomolecular chemistry. 18(36):7090-7093 [DOI] 10.1039/d0ob01678k. [PMID] 32915183.
2019
B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.
Organic letters. 21(4):984-988 [DOI] 10.1021/acs.orglett.8b03959. [PMID] 30693779.
2019
Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C-H Bonds of Drug Molecules.
Journal of the American Chemical Society. 141(37):14570-14575 [DOI] 10.1021/jacs.9b08662. [PMID] 31480842.
2019
Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst.
Journal of the American Chemical Society. 141(10):4199-4203 [DOI] 10.1021/jacs.8b13757. [PMID] 30786707.
2019
Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis.
Journal of the American Chemical Society. 141(29):11414-11419 [DOI] 10.1021/jacs.9b05556. [PMID] 31280564.
2018
C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.
Journal of the American Chemical Society. 140(33):10593-10601 [DOI] 10.1021/jacs.8b06699. [PMID] 30045617.
2017
Enantioselective Direct Mannich-Type Reactions Catalyzed by Frustrated Lewis Acid/Brønsted Base Complexes.
Angewandte Chemie (International ed. in English). 56(43):13338-13341 [DOI] 10.1002/anie.201708103. [PMID] 28872740.
2017
Frustrated Lewis Acid/Brønsted Base Catalysts for Direct Enantioselective α-Amination of Carbonyl Compounds.
Journal of the American Chemical Society. 139(1):95-98 [DOI] 10.1021/jacs.6b11908. [PMID] 27983825.
2017
Palladium-Catalyzed Transformations of Alkyl C-H Bonds.
Chemical reviews. 117(13):8754-8786 [DOI] 10.1021/acs.chemrev.6b00622. [PMID] 28697604.
2016
Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Brønsted Base Catalysts.
Angewandte Chemie (International ed. in English). 55(44):13877-13881 [DOI] 10.1002/anie.201608583. [PMID] 27690277.
2015
Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis.
Tetrahedron letters. 56(23):3428-3430 [PMID] 26085694.
2014
Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis.
Journal of the American Chemical Society. 136(37):12872-5 [DOI] 10.1021/ja5075163. [PMID] 25178040.
2014
Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis.
Nature chemistry. 6(2):146-50 [DOI] 10.1038/nchem.1836. [PMID] 24451591.
2014
Palladium(II)-catalyzed enantioselective C(sp³)-H activation using a chiral hydroxamic acid ligand.
Journal of the American Chemical Society. 136(22):8138-42 [DOI] 10.1021/ja504196j. [PMID] 24815880.
2013
Palladium(0)-catalyzed alkynylation of C(sp3)-H bonds.
Journal of the American Chemical Society. 135(9):3387-90 [DOI] 10.1021/ja400648w. [PMID] 23406445.
2013
Understanding the reactivity of Pd(0)/PR3-catalyzed intermolecular C(sp(3))-H bond arylation.
Journal of the American Chemical Society. 135(38):14206-14 [DOI] 10.1021/ja4053416. [PMID] 24003948.
2012
Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.
Journal of the American Chemical Society. 134(45):18570-2 [DOI] 10.1021/ja309325e. [PMID] 23116159.
2012
Pd(II)-catalyzed ortho trifluoromethylation of arenes and insights into the coordination mode of acidic amide directing groups.
Journal of the American Chemical Society. 134(29):11948-51 [DOI] 10.1021/ja305259n. [PMID] 22780303.
2012
Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.
Accounts of chemical research. 45(6):788-802 [DOI] 10.1021/ar200185g. [PMID] 22166158.
2011
Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.
Angewandte Chemie (International ed. in English). 50(39):9081-4 [DOI] 10.1002/anie.201102985. [PMID] 21748831.
2011
Pd(II)-Catalyzed Cross-Coupling of C(sp2 )-H Bonds and Alkyl-, Aryl- and Vinyl-Boron Reagents via Pd(II)/Pd(0) Catalysis.
Chemistry letters. 40(9):1004-1006 [PMID] 23637469.
2011
Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.
Journal of the American Chemical Society. 133(49):19598-601 [DOI] 10.1021/ja207607s. [PMID] 22059375.
2010
Amide-Directed Arylation of sp C-H Bonds using Pd(II) and Pd(0) Catalysts.
Tetrahedron. 66(26):4811-4815 [PMID] 20711414.
2010
Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**.
Israel journal of chemistry. 50(5-6):605-616 [PMID] 21552359.
2010
Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.
Journal of the American Chemical Society. 132(49):17378-80 [DOI] 10.1021/ja108754f. [PMID] 21082838.
2010
Pd(II)-catalyzed olefination of sp3 C-H bonds.
Journal of the American Chemical Society. 132(11):3680-1 [DOI] 10.1021/ja1010866. [PMID] 20187642.
2010
Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.
Angewandte Chemie (International ed. in English). 49(7):1275-7 [DOI] 10.1002/anie.200906104. [PMID] 20082399.
2009
Pd(0)/PR3-catalyzed intermolecular arylation of sp3 C-H bonds.
Journal of the American Chemical Society. 131(29):9886-7 [DOI] 10.1021/ja903573p. [PMID] 19580277.
2008
Pd(II)-catalyzed cross-coupling of sp3 C-H Bonds with sp2 and sp3 boronic acids using air as the oxidant.
Journal of the American Chemical Society. 130(23):7190-1 [DOI] 10.1021/ja801355s. [PMID] 18479089.
2008
Synthesis of beta-, gamma-, and delta-lactams via Pd(II)-catalyzed C-H activation reactions.
Journal of the American Chemical Society. 130(43):14058-9 [DOI] 10.1021/ja807129e. [PMID] 18834119.
2006
Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization.
Organic letters. 8(25):5685-8 [PMID] 17134247.

Grants

Jul 2023 ACTIVE
Catalytic and Stereoselective C-C-Heteroatom Bond Forming Reactions
Role: Principal Investigator
Funding: NATL INST OF HLTH NIGMS
Jul 2023 ACTIVE
Site-Specific Functionalization of Peptides by Cooperative Catalysis
Role: Principal Investigator
Funding: NATL SCIENCE FOU

Education

JSPS Postdoctoral Fellow
2013-2015 · Harvard University
Ph.D
2007-2012 · The Scripps Research Institute

Contact Details

Phones:
Business:
(561) 228-2476
Emails:
Business:
wasam@ufl.edu
Lab Admin Coordinator II:
Autumn M Bros
View Profile
Addresses:
Business Street:
130 SCRIPPS WAY # 1A2
JUPITER FL 33458