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Asymmetric Synthesis of Homoallylic Alcohols Featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis

preprint
submitted on 16.04.2021, 21:58 and posted on 19.04.2021, 10:19 by Sijing Xue, Bart Limburg, Debasish Ghorai, Jordi Benet Buchholz, Arjan. W. Kleij
Dual palladium/photoredox-catalysis provides an effective method for the asymmetric synthesis of vicinal a,b-tri/tetra- or a,b-tetra-substituted homoallylic alcohols. Regio- and enantioselective decarboxylative allylic alkylation of vinyl cyclic carbonates is reported using Hantzsch type esters as radical precursors. The developed methodology combines the use of versatile and accessible reagents and can be operated under mild reaction conditions giving the target molecules in appreciable to good yields, high branch-selectivity and appreciable enantiomeric ratios of up to 94:6. This protocol marks a rare example of the use of prochiral electrophiles for the creation of vicinal congested carbon centers.

Funding

Cerca program/Generalitat de Catalunya, ICREA, MINECO (CTQ2017-88920-P)

AGAUR (2017-SGR-232)

Ministerio de Ciencia e Innovación (Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S)

Marie Curie individual fellowship (PHOTOCARBOX grant agreement 889754)

Beatriu de Pinos postdoctoral funding from AGAUR (2018-BP-00243)

History

Email Address of Submitting Author

blimburg@iciq.es

Institution

ICIQ

Country

Spain

ORCID For Submitting Author

0000-0002-7996-2485

Declaration of Conflict of Interest

The authors declare no conflict of interest

Version Notes

initial version 1

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