Remarkable enhancement effect of potassium tert-butoxide/THF solution in base-induced Sommelet-Hauser rearrangements

Tetrahedron

Volumn 66, Issue 48, 2010, Pages 9389-9395

  Tayama, Eiji ^a   Takedachi, Keisuke ^a   Iwamoto, Hajime ^a   Hasegawa, Eietsu ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Amino acid; Ammonium salt; Pericyclic reaction; Rearrangement; Ylide

Indexed keywords

ACETIC ACID DERIVATIVE; AMINE; AMINO ACID; AMMONIA; BASE; BENZYL 2 (DIMETHYLAMINO) 3 PHENYLPROPANOIC ACID; BENZYL(DIMETHYLAMINO)(2 METHYLPHENYL)ACETIC ACID; N,N DIETHYL 2 DIMETHYLAMINO 2 (2 METHYLPHENYL)ACETAMIDE; N,N DIETHYL 2 DIMETHYLAMINO 3 PHENYLPROPANAMIDE; N,N DIMETHYL 1 (2 METHYLPHENYL) 2 OXO 2 (PYRROLIDIN 1 YL)ETHANAMINE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; PROPIONIC ACID DERIVATIVE; TERT BUTYL (3 CHLORO 2 METHYLPHENYL)(DIMETHYLAMINO)ACETIC ACID; TERT BUTYL (4 CHLORO 2 METHYLPHENYL)(DIMETHYLAMINO)ACETIC ACID; TERT BUTYL (5 CHLORO 2 METHYLPHENYL)(DIMETHYLAMINO)ACETIC ACID; TERT BUTYL (DIMETHYLAMINO)(2 METHYLPHENYL)ACETIC ACID; TERT BUTYL (DIMETHYLAMINO)(2,3 DIMETHYLPHENYL)ACETIC ACID; TERT BUTYL (DIMETHYLAMINO)(2,4 DIMETHYLPHENYL)ACETIC ACID; TERT BUTYL 2 (DIMETHYLAMINO) 3 (2 METHYLPHENYL)PROPANOIC ACID; TERT BUTYL 2 (DIMETHYLAMINO) 3 (3 METHYLPHENYL)PROPANOIC ACID; TERT BUTYL 2 (DIMETHYLAMINO) 3 (4 METHOXYPHENYL)PROPANOIC ACID; TERT BUTYL 2 (DIMETHYLAMINO) 3 (4 METHYLPHENYL)PROPANOIC ACID; TERT BUTYL 2 (DIMETHYLAMINO) 3 PHENYLPROPANOIC ACID; TERT BUTYL 3 (2 CHLOROPHENYL) 2 (DIMETHYLAMINO)PROPANOIC ACID; TERT BUTYL 3 (3 CHLOROPHENYL) 2 (DIMETHYLAMINO)PROPANOIC ACID; TERT BUTYL 3 (4 CHLOROPHENYL) 2 (DIMETHYLAMINO)PROPANOIC ACID; TERT BUTYL(DIMETHYLAMINO)(2,5 DIMETHYLPHENYL)ACETIC ACID; TERT BUTYL(DIMETHYLAMINO)(5 METHOXY 2 METHYLPHENYL)ACETIC ACID; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SOMMELETE HAUSER REARRANGEMENT;

EID: 78049458125     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.105     Document Type: Article

References (32)

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32. 1H NMR comparison with the (S)-authentic sample. The configuration of 8a and 9a were determined by the analogy with 8b and 9b. For experimental details, see Supplementary data.