Enantioselective aza-Friedel-Crafts reaction catalyzed by a water inclusion complex of O,O′-diacyl tartaric acid

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1203-1205

  Ube, Hitoshi ^a   Fukuchi, Satoko ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; O,O' DI 3 TOLUOYL DEXTRO TARTARIC ACID; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77956696328     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.012     Document Type: Article

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35. Compound 3 was purchased from Aldrich Chemical Co. (Catalogue No. 302813-5G) and used as it was.
36. 2O (0.01 mmol) was added to the solution in one portion. After completion of the reaction (monitored by TLC), a few drops of triethylamine was added to the reaction mixture. The mixture was directly purified by silica-gel column chromatography to yield product 4a.
37. The monohydrate of 3 was purchased from Aldrich Chemical Co. (Catalogue No. 108081-5G) and used as it was.
38. The reaction did not proceed at all without 3 in either presence or absence of MS 4 under similar reaction conditions.
39. 3.
40. 2O which was employed as the catalyst.
41. The catalysts having lower water content were prepared from synthetic O,O′-di-p-toluoyl-d-tartaric acid which included 0.3 equiv of water.