NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

Copyright © 2020, Davies et al.; licensee Beilstein-Institut..

The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable diastereocontrol (typically ≈70:30 dr) and excellent enantioselectivity, and they can be isolated in moderate to good yield as a single diastereoisomer.

Medienart:

E-Artikel

Erscheinungsjahr:

2020

Erschienen:

2020

Enthalten in:

Zur Gesamtaufnahme - volume:16

Enthalten in:

Beilstein journal of organic chemistry - 16(2020) vom: 16., Seite 1572-1578

Sprache:

Englisch

Beteiligte Personen:

Davies, Alyn T [VerfasserIn]
Greenhalgh, Mark D [VerfasserIn]
Slawin, Alexandra M Z [VerfasserIn]
Smith, Andrew D [VerfasserIn]

Links:

Volltext

Themen:

Enantioselective catalysis
Formal [2 + 2] cycloaddition
Journal Article
N-heterocyclic carbene
Ring opening
Trifluoromethyl group

Anmerkungen:

Date Revised 03.02.2021

published: Electronic-eCollection

Citation Status PubMed-not-MEDLINE

doi:

10.3762/bjoc.16.129

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM312803125