CaltechAUTHORS
Published May 11, 2022 | Version Supplemental Material + Accepted Version
Journal Article Open

Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers

Creators

  • 1. ROR icon California Institute of Technology

Abstract

An enantioselective iridium-catalyzed allylic alkylation of malonates with trisubstituted allylic electrophiles to form all-carbon quaternary stereocenters is reported. This reaction proceeds at ambient temperature and enables the preparation of a wide range of enantioenriched products in up to 93% yield and 97% ee. The quaternary products can be readily converted to several valuable building blocks such as vicinal quaternary products and β-quaternary acids.

Additional Information

© 2022 American Chemical Society. Received 18 March 2022. Published online 27 April 2022. Published in issue 11 May 2022. The authors would like to thank Dr. Mona Shagholi for mass spectrometry assistance and Dr. Scott Virgil for assistance with instrumentation. The NIH-NIGMS (R01GM080269 and R35GM145239) and Caltech are thanked for their support of our research program. E.F.H. and Z.P.S. would like to thank the NSF GRFP for funding. Author Contributions. F.A.M. and E.F.H. contributed equally. The authors declare no competing financial interest.

Attached Files

Accepted Version - nihms-1874509.pdf

Supplemental Material - ja2c02960_si_001.pdf

Files

ja2c02960_si_001.pdf

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Additional details

Identifiers

Eprint ID
114828
Resolver ID
CaltechAUTHORS:20220520-649526000

Related works

Describes
https://resolver.caltech.edu/CaltechAUTHORS:20220322-742009000 (URL)

Funding

NIH
R01GM080269
NIH
R35GM145239
Caltech
NSF Graduate Research Fellowship

Dates

Created
2022-05-20
Created from EPrint's datestamp field
Updated
2023-07-06
Created from EPrint's last_modified field