Synthesis of W‐Phos Ligand and Its Application in the Copper‐Catalyzed Enantioselective Addition of Linear Grignard Reagents to Ketones

The asymmetric catalytic addition of linear Grignard reagents to ketones has been a long‐standing challenge in organic synthesis. Herein, a novel family of PNP ligands (W‐Phos) was designed and applied in copper‐catalyzed asymmetric addition of linear Grignard reagents to aryl alkyl ketones, allowin...

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Veröffentlicht in:	Angewandte Chemie International Edition Jg. 61; H. 29; S. e202204443 - n/a
Hauptverfasser:	Luo, Wenjun, Zhang, Li‐Ming, Zhang, Zhan‐Ming, Zhang, Junliang
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	WEINHEIM Wiley 18.07.2022 Wiley Subscription Services, Inc
Ausgabe:	International ed. in English
Schlagworte:	Alcohols Asymmetric Catalysis Asymmetry Chemistry Chemistry, Multidisciplinary Copper Enantiomers Grignard Reagents Ketones Ligands Physical Sciences Reagents Science & Technology Ketones Grignard Reagents ALKYLATION ASYMMETRIC ADDITION CHIRAL TERTIARY ALCOHOLS ALDEHYDES 1,2-ADDITION Alcohols ORGANOBORON REAGENTS ARYL ADDITIONS Asymmetric Catalysis CARBONYL DIALKYLZINC REAGENTS TITANIUM(IV) CATALYST Copper
ISSN:	1433-7851, 1521-3773, 1521-3773
Online-Zugang:	Volltext
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Zusammenfassung:	The asymmetric catalytic addition of linear Grignard reagents to ketones has been a long‐standing challenge in organic synthesis. Herein, a novel family of PNP ligands (W‐Phos) was designed and applied in copper‐catalyzed asymmetric addition of linear Grignard reagents to aryl alkyl ketones, allowing facile access to versatile chiral tertiary alcohols in good to high yields with excellent enantioselectivities (up to 94 % yield, 96 % ee). The process can also be used to synthesize chiral allylic tertiary alcohols from more challenging α,β‐unsaturated ketones. Notably, the potential utility of this method is demonstrated in the gram‐scale synthesis and modification of various densely functionalized medicinally relevant molecules. A novel family of PNP ligands (W‐Phos) was designed and applied in the copper‐catalyzed asymmetric addition of linear Grignard reagents to ketones, allowing ready access to versatile chiral tertiary alcohols in high yields and with excellent enantioselectivities.
Bibliographie:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	1433-7851 1521-3773 1521-3773
DOI:	10.1002/anie.202204443