The major goal of this project is the development of ring-opening metathesis polymerization (ROMP) strategies to an array of high-load oligomers with tunable properties for integrating the science of combinatorial library synthesis with the science of high-throughput chemical library purification. A norbornenyl ring system is utilized as a general chemical tag for incorporation into a wide variety of reagents, scavenging agents, capturing agents for phase-trafficking, soluble supports, and photocleavable linkers. The use of ROM polymerization offers several advantages, including i) selective timing of the ROMP event (in situ ROMP vs. preformed oligomers) tailored to meet the needs of each synthetic sequence, ii) control of bulk physical properties by judicious choice of polymerization conditions, iii) functional group compatibility, and iv) the ability to produce high-load soluble oligomers and polymers.
Current efforts have generated soluble oligomeric acid chloride scavengers (OSC, OBAC, OPC), soluble supports, benzylating agents (OBA and OBSPc), coupling reagents, and other enabling reagents. Moreover, this work has demonstrated a new concept whereby polymer-on-polymer (PoP) processes are possible as evident by the first PoP Mitsunobu reaction.
Capture-ROMP-Release: Org. Lett. 2002, 4, 1007-1010.
Capture-ROMP-Release 2: Tetrahedron.
Lett.
2003, 44, 7187-7190. Scavenge-ROMP-Filter: Org.
Lett. 2002, 4, 1847-1849. ROMpt-Synthesis: Org. Lett.
2003, 5, 15-18. OSC: Org. Lett. 2003, 5, 105-107.
OBAC: Org. Lett. 2003, 5, 4241-4244.
OBA: Org. Lett. 2004, 6, 2657-2660.
OACC J.
Org Chem. 2004 , 69, 8340-8344.
OTTP and HO-DEAD J. Am. Chem.
Soc. 2005, 127(1), 52-53.
Reviews: Aldrichimica Acta 2005,
38, 3-16.
