Erratum: Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds (Angewandte Chemie - International Edition (2005) 44 (6219-6222) DOI: 10.1002/anie.200502134);Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds

Angewandte Chemie - International Edition

Volumn 44, Issue 38, 2005, Pages 6219-6222

  Bartoli, Giuseppe ^a   Bosco, Marcella ^a   Carlone, Armando ^a   Locatelli, Manuela ^a   Melchiorre, Paolo ^a   Sambri, Letizia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

1,3 dicarbonyl compounds; Asymmetric catalysis; Electrophilic substitution; Halogenation; Organocatalysis

Indexed keywords

BROMINE COMPOUNDS; CATALYSIS; CHLORINATION; ESTERS; HALOGENATION; KETONES;

1,3-DICARBONYL COMPOUNDS; ASYMMETRIC CATALYSIS; ELECTROPHILIC SUBSTITUTION; ORGANOCATALYSIS;

ORGANIC COMPOUNDS;

EID: 25844477921     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200690011     Document Type: Erratum

References (44)

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39. The uncatalyzed background chlorination reaction of 1a was demonstrated to proceed to different extents depending on the chlorinating agent; that is, under conditions of 1:1 1a/3, in toluene for 3 h at room temperature, the conversion of 1a is 100% with 3a, 58% with 3c, and 12% with 3d.
40. It was reported that the use of trichloroquinolinone 3d in the asymmetric catalytic α-chlorination of acid halides resulted in poor chemical and optical yields; see reference [8b].
41. 3 represents a key step of catalysis, see the α-chlorination of acid halides in reference [8b].
42. 3 on reactivity is more appreciable with less-reactive substrates such as linear β-keto esters. The effects of various bases on the asymmetric halogenation were evaluated (see Supporting Information).
43. The absolute configurations of 2a-b and 2e were determined to be S by comparison of the specific optical rotations with those reported in the literature. All other absolute configurations were assigned by analogy. Although it is premature to provide a detailed mechanistic explanation at this level, the sense of stereochemical induction suggests the formation of a BQd-enolate ionic complex in which the Re face is effectively shielded by the chiral organocatalyst.
44. The use of different brominating agents such as N-bromosuccinimide and 2,4,4,6-tetrabromo-2,5-cyclohexadione resulted in very low enantioselectivities.