biostudies-literatureChen WChina Scholarship CouncilDeutsche ForschungsgemeinschaftAlexander von Humboldt-StiftungEinstein Stiftung Berlin15126-15129https://www.ebi.ac.uk/biostudies/studies/S-EPMC7756304biostudies-literatureUnknown26(66)An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi-Jørgensen catalyst and can be removed by a boron Lewis acid mediated C-C bond cleavage. The robust two-step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde.Chemistry (Weinheim an der Bergstrasse, Germany)The Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate.PMC7756304Oe 249/18-1Fang HXie KChen WOestreich MfalseThe Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate.An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi-Jørgensen catalyst and can be removed by a boron Lewis acid mediated C-C bond cleavage. The robust two-step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde.2020-01-01T00:00:00Z2020 Nov2025-04-22T21:50:45.639Z2025-04-06T03:47:59.627ZS-EPMC77563043280873110.1002/chem.202003764