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Metal-Catalyzed N–H and O–H Insertion from α-Diazocarbonyl Compounds

Beiträge zur organischen Synthese, Bd. 79

Yuling Hu

ISBN 978-3-8325-4864-3
208 pages, year of publication: 2019
price: 47.00 €
Transition-metal catalyzed X-H insertions fromlinebreak α-diazocarbonyl compounds represent one of the most efficient approaches to form C-X bonds. The presented thesis is based on the synthesis and application oflinebreak α-diazocarbonyl compounds in metal-catalyzed N-H insertion and the chemoenzymatic synthesis of heterocycles via a [Cu]/[Rh] catalyzed intramolecular O-H insertion. In the first part, a straightforward approach via the Wittig reaction, γ-Umpolung addition and diazo transfer reaction allowed the synthesis of unsaturated α-diazocarbonyl compounds with ease. In the second part, the newly synthesized (Rp)-pseudo-ortho [2.2]paracyclophane-based bisoxazoline ligands presented superior reactivity. The obtained δ-aminolinebreak α,β-unsaturated carboxylic esters were used to synthesize hexahydroindoles, which are key intermediates in the synthesis route of Rostratin B-D. Additional investigation of α-diazocarbonyl compounds led to the enzymatic synthesis of O-Heterocycles. With the employment of enantiopure starting material obtained from ketoreductase LbADH, the enantioselectivity of each diastereomer from the O-H insertion product have been effectivity improved.

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Table of contents (PDF)

Keywords:

  • α-diazocarbonyl compounds
  • carbene insertion
  • [2.2]paracyclophane-based bisoxazoline ligands
  • methodology
  • enzymatic synthesis

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