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Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group

13 June 2022, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

The catalytic enantioselective synthesis of α-chiral alkenes and alkynes represents a powerful strategy for rapid generation of molecular complexity. Herein, we report a transient directing group facilitated site-selective palladium-catalyzed reductive Heck-type hydroalkenylation and hydroalkynylation of alkenylaldehyes using alkenyl and alkynyl bromides, respectively, allowing for construction of a stereocenters at the δ position with respect to the aldehyde.

Keywords

palladium
alkene functionalization
hydroalkenylation
hydroalkynylation
transient directing group

Supplementary materials

Title
Description
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Title
Supporting Info
Description
Experimental procedures, characterization data for new compounds, copies of NMR spectra and SFC chromatograms, X-ray crystallographic data
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Title
3ak_CIF
Description
Crystallographic information file for compound 3ak
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Now Published

Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group: Catalyst Generality through Rigidification** [opens in a new tab]
Amit Kumar Simlandy, Turki M. Alturaifi, Johny M. Nguyen, Lucas J. Oxtoby, Quynh Nguyen Wong, Jason S. Chen, Peng Liu, Keary M. Engle journal article
Angewandte Chemie International Edition , Volume 62, Issue 29
Online publication date: Jun 07, 2023

Version History

Jun 13, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-h8w0k
D O I: 10.26434/chemrxiv-2022-h8w0k [opens in a new tab]

Funding

National Institutes of Health
R35GM125052
National Science Foundation
DGE-184247

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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