The Phosphonate‐Phosphate‐ and Phosphate‐Phosphonate Rearrangement and Their Applications, 4 . Deprotonation of Secondary Benzylic Phosphates — Configurationally Stabile Benzylic Carbanions with a Diethoxyphosphoryloxy Substituent and Their Rearrangement to Optically Active Tertiary α‐Hydroxyphosphonates | Zendy

Hammerschmidt Friedrich | Zendy; Schmidt Susanne | Zendy

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The Phosphonate‐Phosphate‐ and Phosphate‐Phosphonate Rearrangement and Their Applications, 4 . Deprotonation of Secondary Benzylic Phosphates — Configurationally Stabile Benzylic Carbanions with a Diethoxyphosphoryloxy Substituent and Their Rearrangement to Optically Active Tertiary α‐Hydroxyphosphonates

Author(s) -

Hammerschmidt Friedrich,

Schmidt Susanne

Publication year - 1996

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19961291217

Subject(s) - chemistry , phosphonate , deprotonation , substituent , enantiomer , phosphate , medicinal chemistry , optically active , ether , enantiomeric excess , carbanion , walden inversion , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , ion

Optically active alcohols (ee ≥ 98%) such as 1‐phenylpropanol, 1‐(2‐naphthyl)ethanol, 1‐tetralol, and 1‐indanol were transformed into diethyl phosphates 7a–d . s BuLi/TMEDA — induced phosphate—phosphonate rearrangement in diethyl ether furnished tertiary α‐hydroxyphosphonates 8a–d of high enantiomeric purity (ee 94–98%) in yields of 43–83% with retention of configuration. The enantiomeric excesses were determined by using homochiral t ‐butyl(phenyl)phosphinothioic acid as chiral solvating agent.

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