Aldehyde Carboxylation: A Concise DFT Mechanistic Study and a Hypothetical Role of CO (2) in the Origin of Life

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Carbon dioxide is arguably one of the most stable carbon-based molecules, yet enzymatic carbon fixation processes enabled the sustainable life cycle on Earth. Chemical reactions involving CO (2) -functionalization often suffer from low efficiency with highly reactive substrates. We recently reported mild carboxylation of aldehydes to furnish -keto acids - a building block for chiral -amino acids via reductive amination. Here, we discuss potential reaction mechanisms of aldehyde carboxylation reactions based on two promoters: NHCs and KCN in the carboxylation reaction. New DFT mechanistic studies suggested a lower reaction barrier for a CO (2) -functionalization step, implying a potential role of CO (2) in prebiotic evolution of organic molecules in the primordial soup. 1 Introduction: Aldehydes, Benzoins, Carboxylic Acids 2 CO (2) -Activation: NHC, Cyanide, Lewis Acid and Water 3 A Breslow Intermediate: Benzoin Reaction vs. Carboxylation with CO (2) 4 Carboxylation in the Primordial Soup 5 Conclusion
Publisher
GEORG THIEME VERLAG KG
Issue Date
2019-06
Language
English
Article Type
Article
Citation

SYNLETT, v.30, no.9, pp.987 - 996

ISSN
0936-5214
DOI
10.1055/s-0037-1611738
URI
http://hdl.handle.net/10203/262744
Appears in Collection
CH-Journal Papers(저널논문)
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