The proposed research will continue our efforts in development of mild catalytic stereoselective methods for C-C bond formation. In the preceding funding period, reductive coupling reactions were developed wherein C-C bond formation was accomplished under conditions which use a mild silane reducing agent. Our research in this area has largely concluded and we have begun to examine alternate methods for mild C-C bond formation under palladium catalysis. The palladium catalyzed process which we will develop will accomplish C-C bond formation under extraordinarily mild conditions and in a stereoselective fashion. The processes proposed herein will deliver fundamental chiral building blocks which are difficult to access with competitive methodologies. In addition to the methods developed, we will target a number of biologically and structurally interesting natural products. The synthesis endeavors will serve to challenge the efficacy of newly developed methodologies, will highlight their eventual utility to synthetic chemists, and will provide a framework to introduce new synthesis strategies.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
3R01GM064451-07S1
Application #
8448482
Study Section
Synthetic and Biological Chemistry B Study Section (SBCB)
Program Officer
Lees, Robert G
Project Start
2002-07-01
Project End
2012-12-31
Budget Start
2012-04-01
Budget End
2012-12-31
Support Year
7
Fiscal Year
2012
Total Cost
$97,030
Indirect Cost
$35,030
Name
Boston College
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
045896339
City
Chestnut Hill
State
MA
Country
United States
Zip Code
02467
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Le, Hai; Batten, Amanda; Morken, James P (2014) Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin). Org Lett 16:2096-9
Yu, Zhiyong; Ely, Robert J; Morken, James P (2014) Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions. Angew Chem Int Ed Engl 53:9632-6
Ardolino, Michael J; Morken, James P (2014) Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution. J Am Chem Soc 136:7092-100
Ardolino, Michael J; Eno, Meredith S; Morken, James P (2013) Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates. Adv Synth Catal 355:3413-3419
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