KILU seminar: Hydride transfer methodology and synthesis of the octahydronaphthalene class of natural products

The KILU seminar series provides an opportunity to learn about exciting current research. In addition, it is an opportuseries opportunity to meet, exchange ideas and discuss science with colleagues from all around KILU and beyond.

Speaker: Professor Timothy J. Donohoe, Department of Chemistry, University of Oxford, UK

Topic: Hydride transfer methodology and synthesis of the octahydronaphthalene class of natural products

Time and place: February 18 from 15:15-16:00 in lecture hall A at Kemicentrum.

Coffee and cake will be served before the seminar, starting at 14:50, on a first-come, first-served basis (outside lecture hall A).

Abstract 

Recently we made an exciting discovery that opened up many possibilities for hydrogen borrowing alkylation of carbnonyl groups. Ortho-Di-substituted phenyl ketones (C₆Me₅ = Ph*) were introduced as new structural motifs that enabled wide ranging C–C bond formation. The Ph* group now allowed an Ir-catalyzed hydrogen borrowing process to form both α- and b-branched ketones with higher alcohols (1^o and 2^o and diols gave cyclic and acyclic products) and the addition of a chiral ligand led to the isolation of single enantiomers of the products. Note that in all cases, the Ph* group can be easily manipulated after HB alkylation by using a retro-Friedel–Crafts reaction (Ph* release) to produce synthetically useful carboxylic acid derivatives. 

We will also discuss the application of hydrogen borrowing related methods for the synthesis of heterocycles via catalytic dearomatisation sequences and for natural product synthesis using hydride shift methodology.