Enantioselective Catalysts for the Synthesis of α-Substituted Allylboronates-An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols

The use of a convenient protecting group for boronates allows a selective, catalyzed SN2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four po...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2016-01, Vol.55 (4), p.1548-1552
Hauptverfasser: Brauns, Marcus, Muller, Frédéric, Gülden, Daniel, Böse, Dietrich, Frey, Wolfgang, Breugst, Martin, Pietruszka, Jörg
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The use of a convenient protecting group for boronates allows a selective, catalyzed SN2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations. All isomers of homoallylic alcohols are readily accessible. The required enantiomerically pure allylboronates can be prepared by a short and convenient three‐step sequence. The diboron compounds show unprecedented high reactivity. The observed selectivity as well as the relative reactivity were studied by computational methods.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201509198