1. 1. Palladium Catalyzed Organic Transformations

2. Novel catalytic pathway towards functionalized cyclopentanoids
NIIST

3. Pivotal substrate for the methodology
NIIST
Heteroatoms permits rapid escalation of complexity
Strained character of bicyclic system
Heteroatoms are in the allylic position
Internal points of fracture – N-N bond and C-N bond
Easily available and cheap starting materials
Palladium catalyzed reactions
Benign and economic synthetic processes
High level of stereoselectivity
Minimum generation of byproducts

4. Palladium Catalyzed Desymmetrization of Mesobicyclic Hydrazines
NIIST
Synthetic strategy
Palladium Catalyzed Desymmetrization of Mesobicyclic Hydrazines
Stereoselective Synthesis of trans-3,4-Disubstiuted Cyclopentane Derivatives
Iodine or Lewis acid- Sc(OTf)3
Palladium catalyst
Phosphine ligand
Radhakrishnan et al
Org. Biomol. Chem, 2007, 5, 4010
Chem. Commun., 2006, 3510
Adv. Synth. Catal. 2006, 348, 924
Tetrahedron 2006, 62, 3997
Synlett, 2005, 15, 2273.
High level of stereoselectivity
Appendage diversity

5. Diversity oriented synthetic strategy
NIIST
Appendage diversity around a common structural core
Monocentered Nucleophiles
trans-3,4-disubstituted cyclopentene derivatives
Appendage diversity
Skeletal diversity
Stereoselectivity
Diversity oriented
synthetic strategy

6. Alkylidene cyclopentenes-structurally unique products
NIIST
Alkylidene cyclopentenes-structurally unique products
Biologically relevant powerful small molecule library
Unique products in
short number of synthetic steps
Diverse molecular frameworks
and functional groups
Radhakrishnan et al
Tetrahedron, 2008, 9689
New J. Chem., 2007, 31, 237
Org. Biomol. Chem. 2007, 5, 4010
Tet. Lett., 2007, 48, 7225
Synlett, 2006, 15, 2399

7. Structural complexity through tandem reactions
NIIST
Structural complexity through tandem reactions
Radhakrishnan et al
J. Am. Chem. Soc., 2009, 131, 5042.
One pot strategy for cyclopentannulation of heterocycles
Bicentered nucleophiles for ring opening reactions
Common precursors to
Skeletally unique products
Catalyst based control

8. NIIST
Angew. Chem. Int. Ed. 2009,(DOI: /anie ) (Published Online: Jun 29, 2009)