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Enantioselective reformatsky reaction of methyl bromodifluoroacetate
Author(s) -
Braun Manfred,
Vonderhagen Anja,
Waldmüller Delia
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508196
Subject(s) - chemistry , enantioselective synthesis , reagent , adduct , reformatsky reaction , benzaldehyde , amide , alkoxide , recrystallization (geology) , absolute configuration , medicinal chemistry , stereochemistry , catalysis , organic chemistry , paleontology , biology
The Reformatsky reagent 2 generated from methyl bromodifluoroacetate is added to benzaldehyde in the presence of carbinols 3a, b , amino alcohols 3c ‐ g , or amino alkoxide 3h . N ‐Methylephedrine 3c provides the highest enantioselectivity in the formation of the adduct S ‐ 4a (84% ee; >96% after recrystallization) whose absolute configuration is determined by an X‐ray structural analysis of the amide 6 .