Silyl Ethers as Latent Pronucleophiles in Enantioselective Lewis Base Catalyzed Synthesis of Allylic Ethers from Allylic Fluorides DOI
Markus Lange,

Abdulrahman Barakat,

Ivan Vilotijević

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 22, 2024

Abstract Allylic ethers are a common occurrence in natural products, and often used as intermediates target-oriented synthesis. Their synthesis relies on the use of transition-metal catalysts. Here, we report an organocatalytic method for allylation O-centered nucleophiles, Lewis base catalyzed silyl with allylic fluorides. The concept latent pronucleophiles catalysis to overcome limitations substrate scope, even permitting sterically congested O-pronucleophiles. When chiral catalysts used, allyl produced enantioenriched form through kinetic resolution fluorides, where stereoselectivity is determined by catalyst.

Language: Английский

Advances in Transition Metal Catalysis and Organocatalysis Approaches towards Asymmetric Synthesis of β-Amino Acid Derivatives DOI

Farrukh Sajjad,

Shuyue Zhang, Ming‐Hua Xu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 16, 2024

Abstract The stereoselective synthesis of β-amino acids has attracted major attention among the synthetic community in recent years. This review provides an overview important advances chiral acid over past decade. It covers development enantioselective methods using transition-metal complexes or organocatalysts, mainly including catalytic asymmetric hydrogenation, Mannich reaction, multicomponent reactions diazo compounds, and conjugate addition. Additionally, optically active by other approaches are also summarized. 1 Introduction 2 Strategies towards Asymmetric Synthesis β-Amino Acids 2.1 Hydrogenation 2.2 Reaction 2.3 Conjugate Addition 2.4 Multicomponent Reactions 2.5 Miscellaneous 2.5.1 from Chiral Amines 2.5.2 Isoxazolidinones 2.5.3 Other Methodologies 3 Summary Outlook

Language: Английский

Citations

2
Enantioselective Lewis Base Catalysed Allylation of Picoline- and Quinaldine-based Latent Pronucleophiles DOI Creative Commons
Markus Lange,

Nikita Alistratov,

Ivan Vilotijević

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(33), P. 6684 - 6689

Published: Jan. 1, 2024

The concept of latent pronucleophiles enables selective allylation picolines and quinaldines with allylic fluorides in the presence Lewis base catalysts. products are isolated as single regioisomers good yields enantioselectivity.

Language: Английский

Citations

1
Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates DOI Creative Commons
Jordi Duran, Paula Rodríguez,

W.A.H. Vermeer

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 20, 2024

Herein we describe the organocatalytic asymmetric allylic benzylborylation of allyl fluorides with α-silyl benzylboronic esters. The catalytic protocol leverages singular features fluoride as an unconventional leaving group, enabling generation reactive α-boryl carbanion species through desilylative activation. It allows construction a wide set homoallylic benzylated organoboronates bearing two contiguous stereocenters. chiral boronate installed in products serves synthetic lynchpin to construct complex chemical architectures stereospecific manner.

Language: Английский

Citations

0
Silyl Ethers as Latent Pronucleophiles in Enantioselective Lewis Base Catalyzed Synthesis of Allylic Ethers from Allylic Fluorides DOI
Markus Lange,

Abdulrahman Barakat,

Ivan Vilotijević

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 22, 2024

Abstract Allylic ethers are a common occurrence in natural products, and often used as intermediates target-oriented synthesis. Their synthesis relies on the use of transition-metal catalysts. Here, we report an organocatalytic method for allylation O-centered nucleophiles, Lewis base catalyzed silyl with allylic fluorides. The concept latent pronucleophiles catalysis to overcome limitations substrate scope, even permitting sterically congested O-pronucleophiles. When chiral catalysts used, allyl produced enantioenriched form through kinetic resolution fluorides, where stereoselectivity is determined by catalyst.

Language: Английский

Citations

0