Removable Phosphine Reagents for the Mitsunobu Reaction

Abstract

We have developed a novel triphenylphosphine replacement for the Mitsunobu reaction. We have demonstrated that 4-diphenylphosphanyl-benzoic acid 2-trimethylsilanyl-ethyl ester (DPPBE) is an efficient reagent and greatly facilitates the isolation of the desired product.

Mitsunobu reaction - triphenylphosphine - 4-di­phenylphosphanyl-benzoic acid 2-trimethylsilanyl-ethyl ester (DPPBE)

References

<A NAME="RS04502ST-1">1</A> Mitsunobu O. Synthesis  1981,  1 

<A NAME="RS04502ST-2A">2a</A> Hughes DL. Org. React.  1992,  42:  335 

<A NAME="RS04502ST-2B">2b</A> Hughes DL. Org. Prep. Proced. Int.  1996,  28:  127 

<A NAME="RS04502ST-3">3</A> Bernard M. Ford WT. J. Org. Chem.  1983,  48:  326 

<A NAME="RS04502ST-4A">4a</A> Charette AB. Boezio AA. Janes MK. Org. Lett.  2000,  2:  3777 

<A NAME="RS04502ST-4B">4b</A> Charette AB. Janes MK. Boezio AA. J. Org. Chem.  2001,  66:  2178 

<A NAME="RS04502ST-5">5</A> Sieber F. Wentworth P. Toker JD. Wenteorth AD. Metz WA. Reed NN. Janda KD. J. Org. Chem.  1999,  64:  5188 

<A NAME="RS04502ST-6">6</A> Camp D. Jenkins ID. Aust. J. Chem.  1988,  41:  1835 

<A NAME="RS04502ST-7">7</A> Itzstein MV. Morino M. Synth. Commun.  1990,  20:  2049 

<A NAME="RS04502ST-8">8</A> Starkey GW. Parlow JJ. Flynn DL. Bioorg. Med. Chem. Lett.  1998,  8:  2385 

<A NAME="RS04502ST-9">9</A> Itzstein MV. Morino M. Aust. J. Chem.  1983,  36:  557 

<A NAME="RS04502ST-10">10</A>

Phosphoric acid (85%) was used as an external reference.

<A NAME="RS04502ST-11">11</A> This compound was purchased from Aldrich or prepared according to: Herd O. Hebler A. Hingst M. Tepper M. Stelzer O. J. Organomet. Chem.  1996,  522:  69 

<A NAME="RS04502ST-12">12</A> Blinn DA. Button RS. Farazi V. Neeb MK. Tapley CL. Trehearne TE. West SD. Kruger TL. Storhoff BN. J. Organomet. Chem.  1990,  393:  143