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Substituted α‐Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β‐Oxo Thioethers from Weinreb Amides
Author(s) -
Senatore Raffaele,
Ielo Laura,
Urban Ernst,
Holzer Wolfgang,
Pace Vittorio
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800095
Subject(s) - chemistry , carbanion , deprotonation , reagent , aryl , alkyl , sulfur , combinatorial chemistry , organic chemistry , conjugate , ion , mathematical analysis , mathematics
The proper generation of α‐thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β‐oxo thioethers. The procedure is adaptable to alkyl‐ or aryl‐ thiomethyllithium conjugates. It has the advantages of conceptual simplicity and versatility of the addition of organometallics to Weinreb amides with the possibility to fully preserve the optical information contained in the starting materials.