Catalytic Homologation‐Allylboration Sequence for Diastereo‐ and Enantioselective Synthesis of Densely Functionalized β‐Fluorohydrins with Tertiary Fluoride Stereocenters DOI Creative Commons
Qiang Wang,

Lars Eriksson,

Kálmán J. Szabó

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(19)

Published: March 8, 2023

Abstract Homologation of trisubstituted fluoroalkenes followed by allylboration aldehyde, ketone and imine substrates is suitable for synthesis β‐fluorohydrin amine products. In the presence ( R )‐iodo‐BINOL catalyst enantioselectivities up to 99 % can be achieved formation a single stereoisomer with adjacent stereocenters, which one tertiary C−F center.

Language: Английский

Photochemical Carboborylation and Three-component Difunctionalization of α,β-unsaturated Ketones with Boronic Acids via Tosylhydrazones DOI Creative Commons
Álvaro Valdés-Maqueda, Manuel Plaza, Carlos Valdés

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The photochemical carboborylation of α,β-unsaturated tosylhydrazones with boronic acids gives tertiary allylboronates. A one pot sequence involving an aldehyde allylation provides a powerful three-component method for diversity oriented synthesis.

Language: Английский

Citations

0
Synthesis of Carboxylic Acids Containing α-All-Carbon Quaternary Centers from Diazo Compounds and Trialkylboranes DOI
Yuan‐Ze Xu, Yan Xu, Jianbo Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

The construction of C–C bonds to form all-carbon quaternary centers remains a significant challenge in synthetic chemistry. Herein, we report tandem process involving 1,2-migration tetra-coordinated boron intermediate followed by Claisen rearrangement the enolate, achieved through reaction between allyl diazoacetates and trialkylboranes. transformation forms two at carbenic position diazo substrate single-step operation under neutral conditions. Using this method, successfully realized gram-scale formal total synthesis Vincamine, an indole alkaloid with pharmacological activity.

Language: Английский

Citations

0
Catalytic Homologation‐Allylboration Sequence for Diastereo‐ and Enantioselective Synthesis of Densely Functionalized β‐Fluorohydrins with Tertiary Fluoride Stereocenters DOI Creative Commons
Qiang Wang,

Lars Eriksson,

Kálmán J. Szabó

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(19)

Published: March 8, 2023

Abstract Homologation of trisubstituted fluoroalkenes followed by allylboration aldehyde, ketone and imine substrates is suitable for synthesis β‐fluorohydrin amine products. In the presence ( R )‐iodo‐BINOL catalyst enantioselectivities up to 99 % can be achieved formation a single stereoisomer with adjacent stereocenters, which one tertiary C−F center.

Language: Английский

Citations

0