Metal-catalyzed nh and oh insertion from -diazocarbonyl compounds / Yuling Hu.

Format:

Book

Author/Creator:

Hu, Yuling, 1990- author.

Series:

Beiträge zur organischen Synthese

Language:

English

Subjects (All):

Chemistry.

Physical Description:

1 online resource (212 pages) : illustrations

Place of Publication:

Berlin, Germany : Logos Verlag Berlin, [2019]

Summary:

Long description: Transition-metal catalyzed X-H insertions from 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 of 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 (R textsubscriptp)-pseudo-ortho [2.2]paracyclophane-based bisoxazoline ligands presented superior reactivity. The obtained δ-amino 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.

Notes:

Description based on print version record.

PublicationDate: 20190315

ISBN:

3-8325-8754-3