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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

 

作者: Friedrich Hammerschmidt,   Susanne Schmidt,  

 

期刊: Chemische Berichte  （WILEY Available online 1996）
卷期: Volume 129, issue 12  

页码: 1503-1508

 

ISSN:0009-2940

 

年代: 1996

 

DOI:10.1002/cber.19961291217

 

出版商: WILEY‐VCH Verlag

 

关键词: Phosphate—Phosphonate rearrangement;Carbanions, benzylic, configurational stability of;α‐Hydroxyphosphonates, tertiary, chiral, non‐racemic;t‐Butyl(phenyl)phosphinothioic acid, homochiral

 

数据来源: WILEY

 

摘要:

AbstractOptically active alcohols (ee ≥ 98%) such as 1‐phenylpropanol, 1‐(2‐naphthyl)ethanol, 1‐tetralol, and 1‐indanol were transformed into diethyl phosphates7a–d.sBuLi/TMEDA — induced phosphate—phosphonate rearrangement in diethyl ether furnished tertiary α‐hydroxyphosphonates8a–dof high enantiomeric purity (ee 94–98%) in yields of 43–83% with retention of configuration. The enantiomeric excesses were determined by using homochiralt‐butyl(phenyl)phosphinothioic ac

 

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