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Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods

Journal

ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 15, Issue 6, Pages 1236-1242

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/op200195m

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Funding

  1. Robert A. Welch Foundation [F-0038]
  2. NIH-NIGMS [RO1-GM069445]
  3. Eli Lilly and Company
  4. Merck
  5. Johnson and Johnson
  6. Firmenich
  7. Umicore
  8. Takasago
  9. ACS-GCI

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Hydrogenation of pi-unsaturated reactants in the presence of carbonyl compounds or imines promotes reductive C-C coupling, providing a byproduct-free alternative to stoichiometric organometallic reagents in an ever-increasing range of C=X (X = O, NR) additions. Under transfer hydrogenation conditions, hydrogen exchange between alcohols and pi-unsaturated reactants triggers generation of electrophile nucleophile pairs, enabling carbonyl addition directly from the alcohol oxidation level, bypassing discrete alcohol oxidation and generation of stoichiometric byproducts.

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