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2004
Esterification
O 0315
Conversion of α-Haloaldehydes into Acylating Agents by an Internal Redox ReCatalyzed by Nucleophilic Carbenes. — In the presence of a triazolium cata48- 051 action
lyst α-haloaldehydes are transformed into dehalogenated acylation agents. The new
method is applicable to secondary and tertiary bromides. Tertiary bromides require a
longer reaction time. α-Bromoaldehydes are more reactive than chlorinated analogues.
A wide range of nucleophiles can be employed: i.e. primary alcohols, phenols and anilines. The reaction conditions are tolerant of epimerizable stereocenters as is shown for
the reaction of (Ib) with (X). Using a chiral carbene as the catalyst, reaction of (IV) with
meso-hydrobenzoin results in formation of monoacylated diol (XIII). —
(REYNOLDS, N. T.; READ DE ALANIZ, J.; ROVIS*, T.; J. Am. Chem. Soc. 126
(2004) 31, 9518-9519; Dep. Chem., Colo. State Univ., Fort Collins, CO 80523, USA;
Eng.) — Adam
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