Abstract
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.
Original language | English |
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Pages (from-to) | 1469-1473 |
Number of pages | 5 |
Journal | Advanced Synthesis and Catalysis |
Volume | 350 |
Issue number | 10 |
DOIs | |
State | Published - 7 Jul 2008 |
Externally published | Yes |
Keywords
- Alkaloids
- Alkenes
- Asymmetric catalysis
- Cinchona alkaloids
- Isomerization
- Phosphorus heterocycles