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

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

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 2 , 2010

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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.

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

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Article Details

VOLUME: 7
ISSUE: 2
Year: 2010
Page: [110 - 113]
Pages: 4
DOI: 10.2174/157017810790796345
Price: $58