New regiocontrolled synthesis of functionalized pyrroles from 2-azetidinone-tethered allenols

Chemistry - A European Journal

Volumn 14, Issue 2, 2008, Pages 637-643

  Alcaide, Benito ^a   Almendros, Pedro ^b   Carrascosa, Rocío ^a,b   Redondo, María C ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Alienes; Domino reactions; Lactams; Nitrogen heterocycles; Rearrangement

Indexed keywords

ALLENOLS; AZETIDINONE; DOMINO REACTIONS; ENANTIOPURE PYRROLES; PYRROLES; REARRANGEMENT; REGIOCONTROLLED CYCLIZATION;

CYCLIZATION; ENANTIOMERS; REACTION KINETICS; RING OPENING POLYMERIZATION;

AROMATIC HYDROCARBONS;

2 AZETIDINONE; 2-AZETIDINONE; ALCOHOL DERIVATIVE; AZETIDINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; AZETIDINES; CYCLIZATION; MOLECULAR CONFORMATION; PYRROLES; STEREOISOMERISM;

EID: 38149116921     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700788     Document Type: Article

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77. Full spectroscopic and analytical data for compounds not included in the Experimental Section are described in the Supporting Information. It contains compound characterization data, experimental procedures for compounds 2a-h, (R)- and (5)-0-acetylmandelates of compounds (+)-2g, 3a-h, 5a-h, 6a-h. (-)-7b. (-)-8b. 12b-e. 15b-d, and 15f-h, mechanistic explanation for the direct formation of pyrroles 12 from phenyl alienes 3 through e/ido-cyclization (Scheme S8). and rationalization for the direct formation of pyrroles 15 from alienes 6 (Scheme S9).