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 | |
| Publication status | Published - 17 Sep 2019 |
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Keywords
- Asymmetric Synthesis
- Carbon monoxide surrogates
- Hydroformylation
- Regioselectivity
- Rhodium
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CO-free Enantioselective Hydroformylation of Functionalised Alkenes: Using a Dual Catalyst System to Give Improved Selectivity and Yield. / Pittaway, Rachael; Dingwall, Paul; Fuentes, José A.; Clarke, Matthew L.
In: Advanced Synthesis and Catalysis, Vol. 361, No. 18, 17.09.2019, p. 4334-4341.Research output: Contribution to journal › Article
TY - JOUR
T1 - CO-free Enantioselective Hydroformylation of Functionalised Alkenes: Using a Dual Catalyst System to Give Improved Selectivity and Yield
AU - Pittaway, Rachael
AU - Dingwall, Paul
AU - Fuentes, José A.
AU - Clarke, Matthew L.
PY - 2019/9/17
Y1 - 2019/9/17
N2 - 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.
AB - 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.
KW - Asymmetric Synthesis
KW - Carbon monoxide surrogates
KW - Hydroformylation
KW - Regioselectivity
KW - Rhodium
UR - http://www.scopus.com/inward/record.url?scp=85070774541&partnerID=8YFLogxK
U2 - 10.1002/adsc.201900640
DO - 10.1002/adsc.201900640
M3 - Article
AN - SCOPUS:85070774541
VL - 361
SP - 4334
EP - 4341
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 18
ER -