Titanium-mediated domino radical cyclization/βelimination of phosphine oxides

Angewandte Chemie - International Edition

Volumn 43, Issue 32, 2004, Pages 4220-4222

  Leca, Dominique ^a   Fensterbank, Louis ^a   Lacôte, Emmanuel ^a   Malacria, Max ^a  

^a CNRS   (France)

Author keywords

Cyclization; Domino reactions; Phosphorus; Radical reactions; Titanium

Indexed keywords

REACTION KINETICS; TITANIUM;

ELIMINATION REACTIONS; PHOSPHINE OXIDES;

PHOSPHORUS COMPOUNDS;

BORANE DERIVATIVE; ESTER; OXYGEN; PHOSPHINE OXIDE DERIVATIVE; RADICAL; SULFOXIDE; TIN; TITANIUM;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; REDUCTION KINETICS; RING OPENING;

EID: 4544291161     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460099     Document Type: Article

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38. Note that phosphinoyl derivatives have one additional advantage: when subjected to the titanium-mediated sequence, sulfoxides lead to both low yields and reduction to the corresponding sulfides. We did not study this further, but to some extent this precludes part of the asymmetric version, since initial reduction would eliminate any stereochemical information present on the sulfur atom.