From Cationic to Anionic Helicenes: New Reactivity through Umpolung

Conreaux, David; Mehanna, Nathalie; Herse, Christelle; Lacour, Jérôme

doi:10.1021/jo200071n

Scientific article

English

From Cationic to Anionic Helicenes: New Reactivity through Umpolung

ContributorsConreaux, David; Mehanna, Nathalie; Herse, Christelle; Lacour, Jérôme

Published inJournal of organic chemistry, vol. 76, no. 8, p. 2716-2722

Publication date2011

Abstract

Using a two-step reduction/metalation procedure, highly stable chiral carbenium ions are transformed into reactive carbanion intermediates. Interesting polar ketone and thioamide products are the results of this umpolung that occurs with complete retention of configuration of the helical backbone.

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

CONREAUX, David et al. From Cationic to Anionic Helicenes: New Reactivity through Umpolung. In: Journal of organic chemistry, 2011, vol. 76, n° 8, p. 2716–2722. doi: 10.1021/jo200071n

Article (Published version)

Identifiers

PID : unige:14940
DOI : 10.1021/jo200071n

ISSN of the journal0022-3263

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From Cationic to Anionic Helicenes: New Reactivity through Umpolung

Using a two-step reduction/metalation procedure, highly stable chiral carbenium ions are transformed into reactive carbanion intermediates. Interesting polar ketone and thioamide products are the results of this umpolung that occurs with complete retention of configuration of the helical backbone.

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