trans-(-)-Limonene oxide is a valuable chiral terpene oxide building block.Used in the synthesis of Phosphorus Incorporation (PI) reagents, as a biologically sourced component of polycarbonate polymers, and as a building block for synthetic applications requiring a reactive epoxide or alkene.
Journal of the American Chemical Society, 141(19), 7709-7714 (2019-04-30)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated
Journal of the American Chemical Society, 141(24), 9548-9554 (2019-06-11)
Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely, bimetallic radical redox-relay, in the
Journal of the American Chemical Society, 139(6), 2484-2503 (2017-01-18)
This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C-C bonds. Optimization of a reductive diene cyclization led to the development of an intermolecular cross-coupling of electronically-differentiated donor
Synthesis and self-assembly of biobased poly(limonene carbonate)-block-poly(cyclohexene carbonate) diblock copolymers prepared by sequential ring-opening copolymerization.
Journal of the American Chemical Society, 142(12), 5785-5792 (2020-02-29)
Phosphorus Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct
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