Experimental and theoretical investigation in the stereoselective synthesis of P-stereogenic phosphine oxides - Archive ouverte HAL Access content directly
Journal Articles Chemistry - A European Journal Year : 2015

Experimental and theoretical investigation in the stereoselective synthesis of P-stereogenic phosphine oxides

Abstract

An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides has been developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as the chiral auxiliary. The method relies on three key steps: 1) Highly diastereoselective formation of PV oxazaphospholidine, rationalized by a theoretical study; 2) highly diastereoselective ring-opening of the oxazaphospholidine oxide with organometallic reagents that takes place with inversion of configuration at the P atom; 3) enantioselective synthesis of phosphine oxides by cleavage of the remaining P[BOND]O bond. Interestingly, the use of a PIII phosphine precursor afforded a P-epimer oxazaphospholidine. Hence, the two enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor, which constitutes a clear advantage for the stereoselective synthesis of sterically hindered phosphine oxides.

Dates and versions

hal-01311828 , version 1 (04-05-2016)

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L. Copey, L. Jean-Gérard, E. Framery, G. Pilet, V. Robert, et al.. Experimental and theoretical investigation in the stereoselective synthesis of P-stereogenic phosphine oxides. Chemistry - A European Journal, 2015, 21 (25), pp.9057-9061. ⟨10.1002/chem.201501324⟩. ⟨hal-01311828⟩
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