Optically Active 6-Membered P-Heterocycles: 1-Phenyl-1,2-Dihydrophosphinine Oxide and 1-Phenyl-3-Diphenylphosphinoyl-1,2,3,6-Tetrahydrophosphinine Oxide

Title: Optically Active 6-Membered P-Heterocycles: 1-Phenyl-1,2-Dihydrophosphinine Oxide and 1-Phenyl-3-Diphenylphosphinoyl-1,2,3,6-Tetrahydrophosphinine Oxide

Volume: 7 Issue: 2

Author(s): Viktoria Ujj, Andrea Kerenyi, Andrea Laki, Elemer Fogassy and Gyorgy Keglevich

Affiliation:

Keywords: Resolution, dihydrophosphinine oxide, tetrahydrophosphinine oxide, Michael addition, platinum complex

Abstract: The antipodes of racemic 1-phenyl-1,2-dihydrophosphinine oxides 1A and 1B were separated by resolution via formation of a diastereomeric complex using ( – )-(2R,3R)-α,α,α,α-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol (spiro-TADDOL) 2. The (+)-antipode of 1-phenyl-3-diphenylphosphinoyl-1,2,3,6-tetrahydrophosphinine oxide 3 was synthesized by the diastereoselective addition of diphenylphosphine oxide to the α,β-double-bond of ( – )-1,2- dihydrophosphinine oxide 1A. The new chiral tetrahydrophosphinine oxide (+)-3 served, after double deoxygenation, as a novel P-chiral bidentate ligand in the corresponding platinum complex.

Cite this article as:

Ujj Viktoria, Kerenyi Andrea, Laki Andrea, Fogassy Elemer and Keglevich Gyorgy, Optically Active 6-Membered P-Heterocycles: 1-Phenyl-1,2-Dihydrophosphinine Oxide and 1-Phenyl-3-Diphenylphosphinoyl-1,2,3,6-Tetrahydrophosphinine Oxide, Letters in Organic Chemistry 2010; 7 (2) . https://dx.doi.org/10.2174/157017810790796345