Enantioselective α-alkylation of phenylacetic acid using a chiral bidentate lithium amide as a chiral auxiliary

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 12, 1997, Pages 2122-2124

  Matsuo, Jun Ichi ^a   Koga, Kenji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Chiral lithium amide; Dilithiated phenylacetic acid; Enantioselective alkylation; substituted phenylacetic acid

Indexed keywords

LITHIUM; PHENYLACETIC ACID;

ALKYLATION; ARTICLE; CHIRALITY; COLUMN CHROMATOGRAPHY; DRUG PURIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0031459901     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.2122     Document Type: Article

References (25)

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15. Judging from the data from runs 1 and 2, partial racemization of the product may be occurring during the reaction in THF. Details are under investigation.
16. By using excess (R)-3, 1-bromo-1,2-diphenylethane was isolated from the reaction mixture.
17. 10 on the alkylation of ketone lithium enolates, addition of lithium bromide caused a dramatic decrease in the enantioselectivity of the reaction (run 7).
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25. The ees of the products were determined by HPLC using a chiral column (Daicel Chiralcel OJ®, hexane/isopropanol/trifluoroacetic acid (9/1/0.01)) for 4a, and a chiral column (Daicel Chiralcel OD-H®, hexane/isopropanol/trifluoroacetic acid (100/2/0.1)) for 4b-d.