Aldol Reactions between L-Erythrulose Derivatives and Chiral α-Amino and α -Fluoro Aldehydes: Competition between Felkin–Anh and Cornforth Transition States
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Other documents of the author: Diaz-Oltra, Santiago; Carda, Miguel; Murga, Juan; Falomir, Eva; Marco, J. Alberto
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Aldol Reactions between L-Erythrulose Derivatives and Chiral α-Amino and α -Fluoro Aldehydes: Competition between Felkin–Anh and Cornforth Transition StatesDate
2008Publisher
Wiley-BlackwellISSN
09476539Type
info:eu-repo/semantics/articleSubject
Abstract
Both matched and mismatched diastereoselection have been observed in aldol reactions of a boron
enolate of a protected l-erythrulose derivative with several chiral α-fluoro and α-Amino aldehydes. Strict
adherence ... [+]
Both matched and mismatched diastereoselection have been observed in aldol reactions of a boron
enolate of a protected l-erythrulose derivative with several chiral α-fluoro and α-Amino aldehydes. Strict
adherence to the Felkin–Anh model for the respective transition structures does not account satisfactorily
for all the observed results, as previously observed in the case of α-oxygenatedaldehydes. In some cases,
only the Cornforth model provides a good explanation. The factors that influence this dichotomy are
discussed and a general mechanistic model is proposed for aldol reactions with a-heteroatom-substituted
aldehydes. Additional support for the model was obtained from density functional calculations [-]
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info:eu-repo/semantics/openAccess
info:eu-repo/semantics/openAccess
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