Selective reduction of heteroaromatic ketones: A combinatorial approach

Buitrago, Elina (author): Stockholms universitet,Institutionen för organisk kemi

Lundberg, Helena (author): Stockholms universitet,Institutionen för organisk kemi

Andersson, Hans (author): Stockholms universitet,Institutionen för organisk kemi

Adolfsson, Hans (author): Stockholms universitet,Institutionen för organisk kemi

(creator_code:org_t)

Abstract Subject headings

The enantioselective reduction of prochiral ketones is a most productiveway towards enantio enriched secondary alcohols used in the preparation of biologically active compounds. There are numerous transition metal catalyzed methods for this transformation, particularly based on Ru(II)-and Rh(I)-complexes, but there is a demand for a larger substrate scope. Heteroaromatic ketones are traditionally more challenging substrates. Normally a catalyst is developed for one benchmark substrate, and asubstrate screen is made with the best performing catalyst. Using this methodology, there is a high probability that for different substrates, another catalyst could outperform the one used. We have executed a multiple screen, containing a variety of different ligands together with both Ru and Rh, and heteroaromatic ketones to fine-tune, and find the optimum catalyst depending on the substrate. The acquired information was used to synthesize known, biologically active compounds, where the key reduction steps were performed with high enantioselectivities and yields.

By the author/editor: Buitrago, Elina; Lundberg, Helena; Andersson, Hans; Ryberg, Per; Adolfsson, Hans

About the subject

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

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