The PMe3-catalyzed addition of enantiomerically pure (−)-MenthylO(Ph)P(O)H to electron-deficient alkenes: an efficient way for the preparation of P-stereogenic compounds. Issue 1 (15th January 2017)

• Record Type: Journal Article
• Authors: Saga, Yuta; Mino, Yuka; Kawaguchi, Shin-ichi; Han, Daoqing; Ogawa, Akiya; Han, Li-Biao
• Is Part Of: Tetrahedron, asymmetry. Volume 28:Issue 1(2017)
• Page Start: 84
• Page End: 89
• Publication Date: 2017-01-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2016.11.005
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: A variety of P -stereogenic organophosphorus compounds can be readily prepared by stereoretentive addition. The PMe3 -catalyzed addition of optically active (−)MenthylO(Ph)P(O)H compounds to electron deficient alkenes occur stereospecifically, to produce the corresponding P -stereogenic adducts in high yields. By simply removing the volatiles under vacuum, spectroscopically pure products can be obtained. The present method provides a salt-free clean process for the preparation of P -chiral organophosphorus compounds. Abstract : ( R P )-(−)-Menthyl 2-(diethoxyphosphoryl)ethyl(phenyl)phosphinate: C22 H38 O5 P2 [ α ]D 25 = −18.5 ( c 0.11, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : Ethylene bis-[( R P )-(−)-Menthyl phenylphosphinate]: C34 H52 O4 P2 [ α ]D 26 = −46.3 ( c 0.11, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ), 2P- R, 2P-(1 R, 2 S, 5 R ) Abstract : ( R P )-(−)-Menthyl 2-(dimethoxyphosphoryl)ethyl(phenyl)phosphinate: C20 H34 O5 P2 [ α ]D 25 = −16.7 ( c 0.11, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : ( R P )-(−)-Menthyl 2-(diphenoxyphosphoryl)ethyl(phenyl)phosphinate: C30 H38 O5 P2 [ α ]D 26 = −16.6 ( c 0.12, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : ( R P )-(−)-Menthyl 2-(diphenylphosphoryl)ethyl(phenyl)phosphinate: C30 H38 O3 P2 [ α ]D 26 = −29.3 ( c 0.58, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : (1 R P )-(−)-Menthyl 2-[ethoxy(phenyl)-(2racemic)-phosphoryl]ethyl(phenyl)phosphinate: C26 H38 O4 P2 [ α ]D 26 = −23.5 ( c 0.10, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ), 2P-racemic Abstract : 2-[(−)-Menthoxy(phenyl)-(1 R P )-phosphoryl]ethyl-9, 10-dihydro-9-oxa-10-(2racemic)-phosphaphenanthrene-10-oxide: C30 H36 O4 P2 [ α ]D 26 = −25.9 ( c 0.10, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ), 2P-racemic Abstract : ( R P )-Menthyl 2-cyanoethyl(phenyl)phosphinate: C19 H28 NO2 P [ α ]D 24 = −4.9 ( c 0.53, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : ( R P )-(−)-Menthyl 2-(methoxycarbonyl)ethyl(phenyl)phosphinate: C20 H31 O4 P [ α ]D 24 = −11.5 ( c 0.50, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : ( S P )-(+)-Menthyl 2-(diethoxyphosphoryl)ethyl(phenyl)phosphinate: C20 H34 O5 P2 [ α ]D 26 = +10.1 ( c 0.41, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- S, 1P-(1 S, 2 R, 5 S ) Abstract : (1 S P )-(+)-Menthyl 2-[(−)-menthoxy(phenyl)-(2 R P )-phosphoryl]ethyl(phenyl)phosphinate: C34 H52 O4 P2 [ α ]D 26 = −6.8 ( c 0.11, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ), 2P- S, 2P-(1 S, 2 R, 5 S ) Abstract : ( R P )-(−)-Menthyl benzyl[2-(diethoxyphosphoryl)ethyl]phosphinate: C21 H36 O5 P2 [ α ]D 26 = −33.9 ( c 0.10, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- R, 1P-(1 R, 2 S, 5 R ) Abstract : ( S P )- t -Butyl-[2-(dimethoxyphosphoryl)]phenylphosphine oxide: C14 H24 O4 P2 [ α ]D 26 = −11.0 ( c 0.50, CHCl3 ) Source of chirality: the precursor Absolute configuration: 1P- S