Highly Enantioselective Reformatsky Reaction of Ketones:  Chelation-Assisted Enantioface Discrimination

Highly enantioselective Reformatsky reaction of ketones was accomplished using cinchona alkaloids as chiral ligands. Chelation with the sp2-nitrogen adjacent to the reactive carbonyl center contributed the enantioface discrimination for the high enantioselectivities.

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 18; pp. 3051 - 3054
Main Authors Ojida, Akio, Yamano, Toru, Taya, Naohiro, Tasaka, Akihiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.09.2002
Amer Chemical Soc
Subjects
Alcohols - chemistry
Chemistry
Chemistry, Organic
Chemistry, Pharmaceutical - methods
Cinchona Alkaloids - chemistry
Esters - chemical synthesis
Esters - isolation & purification
Hydroxy Acids - chemical synthesis
Hydroxy Acids - isolation & purification
Ketones - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
BETA-HYDROXY ESTERS
ASYMMETRIC-SYNTHESIS
DIETHYLZINC
COMPLEXES
ALDEHYDES
ADDITIONS
DERIVATIVES
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Summary:Highly enantioselective Reformatsky reaction of ketones was accomplished using cinchona alkaloids as chiral ligands. Chelation with the sp2-nitrogen adjacent to the reactive carbonyl center contributed the enantioface discrimination for the high enantioselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0263189