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Volumn 73, Issue 20, 2008, Pages 7857-7870

Lessons from nature: Biomimetic organocatalytic carbon-carbon bond formations

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETICS; CHEMICAL REACTIONS;

EID: 53849130681     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801374j     Document Type: Review
Times cited : (177)

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    • We presume that the catalyst preferentially reacts with the aliphatic aldehyde 109, not the α,β-unsaturated aldehyde 111, until all of the aliphatic aldehyde 109 has been consumed in the first Michael addition with nitroalkene 110. In this case, the concentration of the iminium-ion activated α,β-unsaturated aldehyde 115 would be low at the beginning of the reaction further explaining the chemoselectivity of the first step.
    • We presume that the catalyst preferentially reacts with the aliphatic aldehyde 109, not the α,β-unsaturated aldehyde 111, until all of the aliphatic aldehyde 109 has been consumed in the first Michael addition with nitroalkene 110. In this case, the concentration of the iminium-ion activated α,β-unsaturated aldehyde 115 would be low at the beginning of the reaction further explaining the chemoselectivity of the first step.
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