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Published January 23, 2020 | Accepted Version + Supplemental Material
Journal Article Open

Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates

Abstract

The enantioselective palladium-catalyzed decarboxylative allylic alkylation of fully substituted α-hydroxy acyclic enol carbonates providing tetrasubstituted benzoin derivatives is reported. Investigation into the transformation revealed that preparation of the starting material as a single enolate isomer is crucial for optimal enantioselectivity. The obtained alkylation products contain multiple reactive sites that can be utilized toward the synthesis of stereochemically rich derivatives.

Additional Information

© 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. Issue Online: 23 January 2020; Version of Record online: 26 November 2019; Accepted manuscript online: 05 November 2019; Manuscript revised: 02 November 2019; Manuscript received: 03 October 2019. We thank NIH-NIGMS (R01GM080269) and Caltech for financial support. E.J.A. thanks the National Science Foundation for a predoctoral fellowship. Larry Henling and Dr. Michael Takase are thanked for X-ray crystallographic structure determination. We thank Dr. David VanderVelde for NMR expertise and Dr. Scott Virgil for instrumentation and SFC assistance.

Attached Files

Accepted Version - Lavernhe_et_al-2019-Advanced_Synthesis___Catalysis.pdf

Accepted Version - nihms-1643083.pdf

Supplemental Material - adsc201901281-s1-si_1.pdf

Supplemental Material - adsc201901281-s2-si_2.cif

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Additional details

Created:
August 22, 2023
Modified:
October 18, 2023