(1-Naphthyl)(trifluoromethyl) <i>O</i>-Carboxy Anhydride as a Chiral Derivatizing Agent: Eclipsed Conformation Enforced by Hydrogen Bonding
Olivier Thillaye du Boullay
Aurélie Alba
Fatima Oukhatar
Blanca Martin-Vaca
Didier Bourissou
10.1021/ol801930m.s001
https://acs.figshare.com/articles/journal_contribution/_1_Naphthyl_trifluoromethyl_i_O_i_Carboxy_Anhydride_as_a_Chiral_Derivatizing_Agent_Eclipsed_Conformation_Enforced_by_Hydrogen_Bonding/2907193
The preparation of the (1-naphthyl)(trifluoromethyl) <i>O</i>-carboxy-anhydride <b>1</b> and its use as a chiral derivatizing agent with several α-chiral primary amines are reported. The very large Δδ<sup>RS</sup> values observed in <sup>1</sup>H NMR have been correlated with a marked preference of the corresponding α-hydroxy-amides for the <i>eclipsed conformation</i>. In comparison, the related <i>O</i>-methylated amides are shown to adopt staggered conformations, which substantiates the critical role of intramolecular hydrogen bonding in maximizing the anisotropic effect.
2008-10-16 00:00:00
naphthyl
Chiral Derivatizing Agent
1 H NMR
Anhydride
preparation
preference
role
intramolecular hydrogen
Hydrogen Bonding
Eclipsed Conformation Enforced
conformation
anisotropic effect
Naphthyl
amide
chiral derivatizing agent
amines
Δδ RS values