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Enantioselective Synthesis of Phospholenes via Asymmetric Organocatalytic Alkene Isomerization
Author(s) -
Hintermann Lukas,
Schmitz Marco
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800226
Subject(s) - chemistry , enantioselective synthesis , cinchona , isomerization , amide , alkene , ene reaction , enantiomer , stereochemistry , hydrolysis , organic chemistry , medicinal chemistry , catalysis
An asymmetric synthesis of the 2,5‐diphenylphosphol‐2‐ene fragment (≥95% ee ) has been realized via enantioselective Cinchona ‐alkaloid catalyzed double bond isomerization of a meso ‐2,5‐diphenylphosphol‐3‐ene amide to a 2,5‐diphenylphosphol‐2‐ene amide (up to 83% ee ), followed by enantiomeric enrichment to ≥95% ee by crystallization. The 2,5‐diphenylphosphol‐2‐ene amide (a cyclic phosphinic acid amide) was hydrolyzed to the 2,5‐diphenylphosphol‐2‐ene acid (a cyclic phosphinic acid) with retention of configuration at C‐5.
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