SF5 -Enolates in Ti(IV)-Mediated Aldol Reactions

Ponomarenko, Maksym V.; Grabowsky, Simon; Pal, Rumpa; Röschenthaler, Gerd-Volker; Fokin, Andrey A. (2016). SF5 -Enolates in Ti(IV)-Mediated Aldol Reactions. Journal of organic chemistry, 81(15), pp. 6783-6791. American Chemical Society 10.1021/acs.joc.6b00946

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The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF5-acetates with aldehydes in the presence of TiCl4 in the non-nucleophilic solvent CH2Cl2. Such bonding is canceled in nucleophilic solvents where opposite cis-stereochemistry is observed. The potential of thus obtained stereoisomeric SF5-aryl acrylates as dipolarophiles in the preparation of SF5-containing heterocycles is demonstrated.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Grabowsky, Simon

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0022-3263

Publisher:

American Chemical Society

Language:

English

Submitter:

Simon Grabowsky

Date Deposited:

06 Feb 2020 11:21

Last Modified:

06 Feb 2020 11:21

Publisher DOI:

10.1021/acs.joc.6b00946

BORIS DOI:

10.7892/boris.138458

URI:

https://boris.unibe.ch/id/eprint/138458

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