Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands

The Journal of Organic Chemistry
Marco OlianaKing Kuok Mimi Hii

Abstract

[reaction: see text] A practical synthesis of optically pure alkylphenylvinylphosphine oxides is described, utilizing a nucleophilic displacement at phosphorus to install the vinyl moiety. The products were used to prepare classes of P-stereogenic aminophosphine (PN) and aminohydroxyphosphine (PNO) ligands. Stereocontrol can be exerted at various stages of the synthesis, to provide specific combinations of chirality in the final product. The effect of the stereogenic phosphorus and match-mismatch of chiralities of PNO ligands were examined in the asymmetric ruthenium-catalyzed hydrogen transfer reduction of three aryl ketones.

References

Jan 4, 2003·Chemical Communications : Chem Comm·Pierluigi BarbaroAntonio Togni

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Citations

Mar 8, 2017·The Journal of Organic Chemistry·Hsin Y Su, Mark S Taylor
Dec 22, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·S HanfD S Wright
Aug 2, 2016·Chemical Society Reviews·Mathieu DutartreSylvain Jugé
Oct 7, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Chunya LiLi-Biao Han
Aug 23, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Carly E AndersonJudith A K Howard
Aug 30, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Mateo AlajarinRaul-Angel Orenes
Jan 7, 2017·Topics in Current Chemistry·E Veerashekhar GoudKari Vijayakrishna
Apr 30, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Sandra HitzelUlrich Siemeling
May 21, 2008·The Journal of Organic Chemistry·Magnus J JohanssonNina Kann
Nov 24, 2011·Organic Letters·Harry AdamsChristopher J A Warner
Aug 26, 2006·The Journal of Organic Chemistry·David J MorrisMartin Wills

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