CO-free Enantioselective Hydroformylation of Functionalised Alkenes: Using a Dual Catalyst System to Give Improved Selectivity and Yield

Rachael Pittaway; Paul Dingwall; José A. Fuentes; Matthew L. Clarke

doi:10.1002/adsc.201900640

CO-free Enantioselective Hydroformylation of Functionalised Alkenes: Using a Dual Catalyst System to Give Improved Selectivity and Yield

Rachael Pittaway, Paul Dingwall, José A. Fuentes, Matthew L. Clarke^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The scope of carbon monoxide-free Asymmetric Transfer HydroFormylation (ATHF) procedures using a highly active single catalyst system derived from 1,2-bis-((2,5)-diphenylphospholano)ethane as chiral ligand has been studied. This reveals some highly successful reactions, but also significant limitations. The development of a new protocol in which a catalyst for formaldehyde decomposition to CO and H₂ is combined with the catalyst of choice for the subsequent asymmetric hydroformylation is described. This enables ATHF reactions that were problematic to be significantly improved. The new method has been used in the synthesis of several key precursors to biologically active molecules.

Original language	English
Pages (from-to)	4334-4341
Journal	Advanced Synthesis and Catalysis
Volume	361
Issue number	18
Early online date	13 Aug 2019
DOIs	https://doi.org/10.1002/adsc.201900640
Publication status	Published - 17 Sep 2019

Keywords

Asymmetric Synthesis
Carbon monoxide surrogates
Hydroformylation
Regioselectivity
Rhodium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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abstract = "The scope of carbon monoxide-free Asymmetric Transfer HydroFormylation (ATHF) procedures using a highly active single catalyst system derived from 1,2-bis-((2,5)-diphenylphospholano)ethane as chiral ligand has been studied. This reveals some highly successful reactions, but also significant limitations. The development of a new protocol in which a catalyst for formaldehyde decomposition to CO and H2 is combined with the catalyst of choice for the subsequent asymmetric hydroformylation is described. This enables ATHF reactions that were problematic to be significantly improved. The new method has been used in the synthesis of several key precursors to biologically active molecules.",

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