Enantioselective [2,3]] sigmatropic rearrangement of α- propargyloxyacetic acids mediated by BuLi-(-)-sparteine complex

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 2, 1998, Pages 335-336

  Manabe, Shino ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

BuLi ( ) sparteine complex; Chiral allenylalcohol; Enantioselective 2,3 sigmatropic rearrangement; propargyloxy acetic acid

Indexed keywords

ALPHA PROPARGYLOXYACETIC ACID; GLYCOLIC ACID DERIVATIVE; LITHIUM; SPARTEINE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0031916818     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.335     Document Type: Article

References (15)

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11. The [2,3] sigmatropic rearrangement of the benzyl prenyl ether 3 mediated by lithiated bis[(S,S)-1-phenylethylamine] did not proceed in THF at -78°C. The starting material 3 was recovered in 92% yield. The same reaction proceeded at 0°C in 81% yield, but the ee of the product was 0%.
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14. a) The [2,3] sigmatropic rearrangement of benzyl prenyl ether 3 mediated by BuLi-(-)-sparteine complex in toluene at -78°C gave the corresponding product 4 in 70% yield, 19% ee (Chart 1);
15. b) Application of BuLi-chiral ligand complex to enantioselective [2,3] sigmatropic rearrangement; Manabe S., Chem. Commun., 737-738 (1997).