Enantioselective reformatsky reaction of methyl bromodifluoroacetate | Zendy

Braun Manfred | Zendy; Vonderhagen Anja | Zendy; Waldmüller Delia | Zendy

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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 .

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