Direct and enantioselective aldol reactions catalyzed by chiral nickel(II) complexes

A direct and asymmetric aldol reaction of N-acylthiazinanethiones with aromatic aldehydes catalyzed by chiralnickel(II) complexes is reported. The reaction gives thecorresponding O-TIPS-protected anti-aldol adducts in highyields and with remarkable stereocontrol and atom economy.Furthermore, the str...

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Bibliographic Details
Authors: Kennington, Stuart C. D.; Teloxa, Saul F.; Mellado Hidalgo, Miguel; Galeote, Oriol; Puddu, Sabrina; Bellido, Marina; Romea, Pedro; Urpí Tubella, Fèlix; Aullón López, Gabriel; Font Bardia, Ma. Mercedes
Format: Article
Status:Published version
Publication date:2021
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/178957
Online Access:https://hdl.handle.net/2445/178957
Access Level:Open access
Keyword:Reacció aldòlica
Síntesi asimètrica
Níquel
Aldol reaction
Asymmetric synthesis
Nickel
Description
Summary:A direct and asymmetric aldol reaction of N-acylthiazinanethiones with aromatic aldehydes catalyzed by chiralnickel(II) complexes is reported. The reaction gives thecorresponding O-TIPS-protected anti-aldol adducts in highyields and with remarkable stereocontrol and atom economy.Furthermore, the straightforward removal of the achiralscaffold provides enantiomerically pure intermediates ofsynthetic interest, which involve precursors for anti-a-amino-b-hydroxy anda,b-dihydroxy carboxylic derivatives. Theoret-ical calculations explain the observed high stereocontrol.