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1. Palladium Catalyzed Organic Transformations

1. Palladium Catalyzed Organic Transformations. NIIST. Novel catalytic pathway towards functionalized cyclopentanoids. NIIST. Pivotal substrate for the methodology. Heteroatoms permits rapid escalation of complexity. Strained character of bicyclic system

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1. Palladium Catalyzed Organic Transformations

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  1. 1. Palladium Catalyzed Organic Transformations

  2. NIIST Novel catalytic pathway towards functionalized cyclopentanoids

  3. NIIST Pivotal substrate for the methodology • 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. 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 Tetrahedron2006, 62, 3997 Synlett, 2005, 15, 2273. • High level of stereoselectivity • Appendage diversity

  5. 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. 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. 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:10.1002/anie.200901939)(Published Online: Jun 29, 2009)

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