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 | Zendy

Bartoli Giuseppe | Zendy; Marcantoni Enrico | Zendy; Sambri Letizia | Zendy; Tamburini Monica | Zendy

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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.

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