Lewis-Base-Catalyzed <i>N</i>-Allylation of Silyl Carbamate Latent Pronucleophiles with Allylic Fluorides

Lange, Markus; Meyer, F. Lorenz; Nosovska, Olena; Vilotijevic, Ivan

doi:10.1021/acs.orglett.3c03228

Org. Lett.

2023

DOI: 10.1021/acs.orglett.3c03228

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Lewis-Base-Catalyzed N-Allylation of Silyl Carbamate Latent Pronucleophiles with Allylic Fluorides

Markus Lange,

F. Lorenz Meyer,

Olena Nosovska

et al.

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2024

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Cited by 4 publications

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Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates

Duran,

Rodríguez,

Vermeer

et al. 2024

Org. Lett.

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

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Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates

Duran,

Rodríguez,

Vermeer

et al. 2024

Org. Lett.

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Enantioselective Lewis base catalysed allylation of picoline- and quinaldine-based latent pronucleophiles

Lange,

Alistratov,

Vilotijevic

2024

Org. Biomol. Chem.

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

Sajjad,

Zhang,

2024

Synthesis

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The stereoselective synthesis of β-amino acids has attracted major attention among the synthetic community in recent years. This review provides an overview of the important advances in chiral β-amino acid synthesis over the past decade. It covers the development of enantioselective methods using transition metal complexes or organocatalysts, mainly including catalytic asymmetric hydrogenation, Mannich reaction, multicomponent reaction of diazo compounds, and conjugate addition. Besides, asymmetric synthesis of optically active β-amino acids from other approaches are also summarized.

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Lewis-Base-Catalyzed N-Allylation of Silyl Carbamate Latent Pronucleophiles with Allylic Fluorides

Cited by 4 publications

References 40 publications

Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates

Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates

Enantioselective Lewis base catalysed allylation of picoline- and quinaldine-based latent pronucleophiles

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

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