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The antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide are highly efficient enantiopure ammonia equivalents for the asymmetric synthesis of β-amino acid derivatives via conjugate addition to α,β- unsaturated esters. 6 Li and 15 N NMR spectroscopic studies of doubly labelled 6 lithium (S)- 15 N-benzyl- 15 N-(α-methylbenzyl)amide in THF at low temperature reveal the presence of lithium amide dimers as the only observable species. Either a monomeric or dimeric lithium amide reactive species can be accommodated within the transition state mnemonic for this class of conjugate addition reaction. This enantiopure lithium amide offers unique opportunities over achiral (e.g. , lithium dibenzylamide) and C 2 -symmetric (e.g., lithium bis-N,N-α-methylbenzylamide) counterparts for further mechanistic study owing to the ready distinction of the various dimers formed. © 2013 Elsevier Ltd. All rights reserved.

Original publication




Journal article


Tetrahedron Asymmetry

Publication Date





947 - 952