Bi(OTf) 3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: Comparison of catalysts and role of Bi(OTf) 3

Journal of Organic Chemistry

Volumn 76, Issue 22, 2011, Pages 9269-9277

  Lambert, R Frederick ^a   Hinkle, Robert J ^a   Ammann, Stephen E ^a   Lian, Yajing ^a   Liu, Jia ^a   Lewis, Shane E ^a   Pike, Robert D ^a  

^a The College of William and Mary   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH TRIFLATE; CATALYTIC QUANTITIES; IN-SITU; ISOLATED YIELD; LEWIS ACID; NMR SPECTROSCOPIC ANALYSIS; ONE POT; SAKURAI;

ALDEHYDES; BISMUTH;

SPECTROSCOPIC ANALYSIS;

2 BUTYL 4 (4 CHLOROBENZYL) 3,6 DIHYDRO 2H PYRAN; 2 BUTYL 6 (4 FLUOROBENZYL) 3,6 DIHYDRO 2H PYRAN; 2 BUTYL 6 ISOPROPYL 3,6 DIHYDRO 2H PYRAN; 2 HEPTYL 6 ISOPROPYL 3,6 DIHYDRO 2H PYRAN; 6 (4 BROMOBENZYL) 2 BUTYL 3,6 DIHYDRO 2H PYRAN; 6 (4 BROMOBENZYL) 2 PHENETHYL 3,6 DIHYDRO 2H PYRAN; 6 (4 CHLOROBENZYL) 2 PHENETHYL 3,6 DIHYDRO 2H PYRAN; 6 (4 FLUOROBENZYL) 2 PHENETHYL 3,6 DIHYDRO 2H PYRAN; 6 BENZHYDRYL 2 BUTYL 3,6 DIHYDRO 2H PYRAN; 6 BENZHYDRYL 2 ETHYL 3,6 DIHYDRO 2H PYRAN; 6 BENZYL 2 BUTYL 3,6 DIHYDRO 2H PYRAN; 6 BENZYL 2 ETHYL 3,6 DIHYDRO 2H PYRAN; 6 BENZYL 2 HEPTYL 3,6 DIHYDRO 2H PYRAN; 6 BENZYL 2 PHENETHYL 3,6 DIHYDRO 2H PYRAN; 6 PHENETHYL 6 ISOPROPYL 3,6 DIHYDRO 2H PYRAN; ALDEHYDE DERIVATIVE; BISMUTH; CARBOXYLIC ACID; DELTA HYDROXYALKENYLSILANE; DIHYDROPYRAN DERIVATIVE; EPOXIDE; INTRAMOLECULAR SILYL MODIFIED SAKURAI; LEWIS ACID; PHENYLACETALDEHYDE; PYRAN DERIVATIVE; SILANE DERIVATIVE; SULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYLTRIFLUOROMETHANESULFONATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; EPOXY COMPOUNDS; LEWIS ACIDS; LEWIS BASES; MAGNETIC RESONANCE SPECTROSCOPY; MESYLATES; MOLECULAR STRUCTURE; PYRANS; SILANES; STEREOISOMERISM;

EID: 81055123740     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201478d     Document Type: Article

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