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Cerium( III ) Chloride Promoted Nucleophilic Addition of Organolithium Reagents to α‐Alkyl‐β‐Ketophosphine Oxides: A New Protocol for the Synthesis of Stereochemically Defined Trisubstituted Olefins
Author(s) -
Bartoli Giuseppe,
Marcantoni Enrico,
Sambri Letizia,
Tamburini Monica
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199520461
Subject(s) - cerium , alkyl , nucleophile , reagent , chemistry , chloride , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
Horner key intermediates 2 for the synthesis of trisbustituted stereochemically defined olefins 3 can be obtained easily be stereoselective alkylation of α‐alkyl‐β‐ketophosphine oxides 1 with RLi·CeCl 3 complexes in THF at −78°C. Decomposition with KH gives trisubstituted alkenes with excellent diastereoselectivity.