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Sequential Elimination–Reduction Reactions Promoted by Samarium Diiodide: Synthesis of 2,3‐Dideuterioesters or ‐amides
Author(s) -
Concellón José M.,
RodríguezSolla Humberto
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20011001)7:19<4266::aid-chem4266>3.0.co;2-8
Subject(s) - samarium diiodide , chemistry , samarium , elimination reaction , reduction (mathematics) , combinatorial chemistry , beta (programming language) , medicinal chemistry , organic chemistry , mathematics , computer science , geometry , programming language
A facile and general sequential elimination/reduction process promoted by samarium diiodide provides an efficient method for synthesizing saturated esters or amides 3 from readily available starting materials. The reaction involves a β ‐elimination of the starting 2‐halo‐3‐hydroxyesters or ‐amides 1 and subsequent 1,4‐reduction of the obtained α , β ‐unsaturated esters or amides in the presence of H 2 O. When D 2 O is used instead of H 2 O, 2,3‐dideuterioesters or ‐amides 4 are isolated. A mechanism is proposed to account for this synthesis.