Tetrahedron Letters p. 2501 - 2504 (1992)
Update date:2022-09-26
Topics:
Ahmar, Mohammed
Bloch, Robert
Mandville, Gerard
Romain, Isabelle
An excellent aldehyde diastereofacial selectivity has been observed during the aldol condensation between the lithium enolate of endo-2-methyl-bicyclo<2.2.1>-hept-5-enyl ethyl ketone 1 and a variety of α-methyl chiral aldehydes. 2-Aryl- and 2-vinylpropionaldehyde gave rise to the predicted syn,syn "Felkin-Anh" diastereoisomers.In contrast β-alkoxy or β-silyloxy α-methyl aldehydes lead to the syn,anti aldols arising from an apparent chelation control.
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