91119-04-9Relevant articles and documents
A ONE-STEP CONVERSION OF ESTERS TO SECONDARY ALCOHOLS WITH LiBH4-RMgX
Comins, Daniel L.,Herrick, James J.
, p. 1321 - 1324 (1984)
A one-pot synthesis of secondary alcohols from esters and LiBH4-RMgX is described.
Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes
Nudelman,Garcia
, p. 1387 - 1394 (2007/10/03)
A tandem reaction between (E)-cinnamaldehyde, 1a, and phenyllithium affording β-substituted dihydrochalcones was recently reported. NMR spectroscopic studies on the reaction mixture, as well as isotopic exchange reactions and trapping of two intermediates, provide clues on the several mechanistic steps of this new reaction. Extended studies revealed that β-alkyl-substituted α,β-unsaturated aldehydes and aliphatic lithium reagents did not afford good yields of the tandem reaction products, while aromatic lithium reagents gave good results. The aggregation features of the aryllithium reagents and the extended charged delocalization effects are considered to promote β-selectivity. This approach provides a convenient route for the synthesis of a wide variety of β-alkyl-substituted dihydrochalcones.