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Showing posts with label University of Toronto. Show all posts
Showing posts with label University of Toronto. Show all posts

Monday 29 August 2016

Multicomponent-Multicatalyst Reactions (MC)2R: Efficient Dibenzazepine Synthesis

Multicomponent-Multicatalyst Reactions (MC)2R: Efficient Dibenzazepine SynthesisJennifer Tsoung, Jane Panteleev, Matthias Tesch, and Mark Lautens
Org. Lett. 201416110-113. DOI:10.1021/ol4030925 .
A RhI/Pd0 catalyst system was applied to the multicomponent synthesis of aza-dibenzazepines from vinylpyridines, arylboronic acids, and amines in a domino process with no intermediate isolation or purification.
5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine (4a)
STR1
1H NMR
(400 MHz, CDCl3) δ 8.66 (d, J = 1.1 Hz, 1H), 7.97 (d, J = 1.8 Hz, 1H), 7.43 – 7.38 (m, 1H), 7.38 – 7.29
(m, 3H), 6.98 (d, J = 8.4 Hz, 2H), 6.57 – 6.51 (m, 2H), 3.33 – 3.21 (m, 2H), 3.09 – 2.99 (m, 2H), 2.26 (s,
3H);
13C NMR (101 MHz, CDCl3) δ 161.7 (q, J = 1.3 Hz), 145.8, 143.6, 143.4 (q, J = 4.0 Hz), 139.7,
139.5, 134.9 (q, J = 3.5 Hz), 130.3, 130.0, 129.9, 128.9, 128.2, 127.7, 125.3 (q, J = 33.1 Hz), 123.4 (q, J =
272.5 Hz), 114.0 (2), 35.9, 29.0, 20.4;
19F NMR (377 MHz, CDCl3) δ -62.0;
IR (NaCl, neat): 3063, 3028,
2926, 2862, 1616, 1506, 1489, 1456, 1435, 1429, 1410, 1339, 1319, 1296, 1267, 1240, 1207, 1165, 1128,
1086, 1036, 978, 947, 930, 910, 895, 808, 772, 756, 737, 721, 704, 687, 664, 646, 627 cm-1;
HRMS (ESI):
calcd for C21H18F3N2 (M+H)+: 355.1422; found. 355.1419.
STR1
Jennifer Tsoung

Jennifer Tsoung

PhD graduate, organic chemistry
Department of Chemistry, University of Toronto

Experience

PhD

University of Toronto
 –  (5 years 2 months)

Research Intern

Kyoto University
 –  (3 months)Kyoto, Japan
Methodology project in asymmetric phase-transfer catalyzed alkylations.

Co-op student

Angiotech
 –  (4 months)Vancouver, Canada Area
Formulation chemistry

Co-op student

Boehringer Ingelheim
 –  (8 months)Montreal, Canada Area
On two hit-to-lead teams working to synthesize analogues of hit compounds for HIV research.

Publications

Diastereoselective Friedel−Crafts Alkylation of Hydronaphthalenes(Link)

The Journal of Organic Chemistry
September 27, 2011
An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intramolecular Friedel-Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated...more

One-Pot Synthesis of Chiral Dihydrobenzofuran Framework via Rh/Pd Catlaysis

Organic Letters
October 12, 2012
A one-pot synthesis of the chiral dihydrobenzofuran framework is described. The method utilizes Rh-catalyzed asymmetric ring opening (ARO) and Pd-catalyzed C-O coupling to furnish the product in excellent enantioselectivity without isolation of intermediates. Systematic metal-ligand studies were carried out to investigate the compatibility of each catalytic system using product enantiopurity as an...more

Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines(Link)

Angew. Chem. Int. Ed
July 19, 2013
A game of dominoes: A synthetic route to aza-dihydrodibenzoxepines is described, through the combination of a Rh-catalyzed arylation and a Pd-catalyzed C-O coupling in a single pot. For the first time, the ability to incorporate a chiral and an achiral ligand in a two-component, two-metal transformation is achieved, giving the products in moderate to good yields, with excellent enantioselectivities.

Multicomponent-multicatalyst reactions (MC)(2)R: efficient dibenzazepine synthesis.

Organic Letters
January 13, 2014
A Rh(I)/Pd(0) catalyst system was applied to the multicomponent synthesis of aza-dibenzazepines from vinylpyridines, arylboronic acids, and amines in a domino process with no intermediate isolation or purification.

Formation of substituted oxa- and azarhodacyclobutanes.

Chemistry - A European Journal
December 6, 2013
The preparation of substituted oxa- and azarhodacyclobutanes is reported. After exchange of ethylene with a variety of unsymmetrically and symmetrically substituted alkenes, the corresponding rhodium-olefin complexes were oxidized with H2O2 and PhINTs (Ts=p-toluenesulfonyl) to yield the substituted oxa- and azarhodacyclobutanes, respectively. Oxarhodacyclobutanes could be prepared with excellent...more

Women in Chemistry group, 2015


Mark Lautens , O.C.

University Professor
J. Bryan Jones Distinguished Professor
AstraZeneca Professor of Organic Chemistry
NSERC/Merck-Frosst Industrial Research Chair



Department of Chemistry
Davenport Chemical Laboratories
80 St. George St.
University of Toronto
Toronto, Ontario
M5S 3H6

Tel: (416) 978-6083
Fax: (416) 946-8185
E-Mail: mlautens@chem.utoronto.ca

Curriculum Vitae

Personal

Place and Date of BirthHamilton, Ontario, CanadaJuly 9, 1959

Education

Harvard UniversityNSERC PDF with D. A. Evans1985 - 1987
University of Wisconsin-MadisonPh.D. with B. M. Trost1985
University of GuelphB.Sc. - Distinction1981

Academic Positions

J. Bryan Jones Distinguished ProfessorUniversity of Toronto2013 - 2018
University ProfessorUniversity of Toronto2012 - present
NSERC/Merck Frosst Industrial Research ChairNSERC/Merck Frosst2003 - 2013
AstraZeneca Professor of Organic SynthesisUniversity of Toronto1998 - present
ProfessorUniversity of Toronto1995 - 1998
Associate ProfessorUniversity of Toronto1992 - 1995
Assistant ProfessorUniversity of Toronto1987 - 1992

Awards & Honors

University of Toronto Alumni Faculty AwardUniversity of Toronto2016
CIC Catalysis AwardCSC2016
Officer of the Order of CanadaGovernor General2014
Killam Research FellowshipCanada Council for the Arts2013-2015
CIC MedalChemical Institute of Canada2013
Fellow of the Royal Society of UKRoyal Society of Chemistry2011
Pedler AwardRoyal Society of Chemistry2011
Senior Scientist AwardAlexander von Humboldt Foundation
Berlin, Aachen and Gottingen
2009-2014
Visiting ProfessorUniversity of Berlin2009
Visiting ProfessorUniversité de Marseilles2008
ICIQ Summer SchoolICIQ Tarragona, Spain2008
Attilio Corbella Summer School ProfessorItalian Chemical Society2007
Arthur C. Cope Scholar AwardAmerican Chemical Society2006
Alfred Bader AwardCanadian Society for Chemistry2006
R. U. Lemieux AwardCanadian Society for Chemistry2004
Solvias PrizeSolvias AG2002
Fellow of the Royal Society of CanadaRoyal Society of Canada2001

Areas of Research Interest and Expertise

  • new synthetic methods
  • metal catalyzed cycloaddition and annulation reactions
  • asymmetric catalysis with focus on rhodium, nickel and palladium catalysts
  • cyclopropane synthesis and reactions
  • hydrometallation reactions
  • reactions of organosilicon and organotin compounds
  • fragmentation reactions
  • new routes to medicinally/biologically interesting compounds
  • heterocycle synthesis using metal catalysts

///////Multicomponent, Multicatalyst Reactions,  (MC)2R,  Dibenzazepine Synthesis, Mark Lautens, University of Toronto , Toronto, Ontario, Jennifer Tsoung