Kinetic resolution of P-chiral tertiary phosphines and chlorophosphines: a new approach to optically active phosphoryl and thiophosphoryl compounds

Perlikowska, Wiesława; Gouygou, Maryse; Daran, Jean‐Claude; Balavoine, G.; Mikołajczyk, M.

doi:10.1016/s0040-4039(01)01694-x

Cited by 21 publications

(15 citation statements)

References 11 publications

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“…The same reaction of (±)-16 and (+)-(R,R)-17 performed under dynamic kinetic resolution conditions (1:1 ratio of reagents) in the presence of chloride ions gave only phosphinoyl chloride 12 with 70% ee [14] (Scheme 10).…”

Section: Synthesis and Reactions Of Halogenidesmentioning

confidence: 99%

“…This procedure involving the application of 17 can be applied to the resolution of P-chiral tertiary phosphines leading to the optically active tertiary phosphine oxides [14]. The starting material, enantiomerically pure 17, was obtained by the iodine oxidation of the (-)--phenylethylammonium salt of (+)-(R)-t-butylphenylphosphinothioic acid (19) under two phase conditions [15] (Scheme 11).…”

Section: Synthesis and Reactions Of Halogenidesmentioning

confidence: 99%

“…The displacement of halogen in P V P-chiral electrophilic halides such as (R P )-and (S P )-t-butylphenylphosphinobromide (14) and t-butylphenylthionophosphinochloride (18) by heteroatom nucleophiles is completely stereoselective leading with clean inversion at phosphorus to chiral phosphinates and related compounds [19] (Schemes 17 and 18).…”

Section: Synthesis and Reactions Of Halogenidesmentioning

confidence: 99%

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The Chemistry of Phosphinic and Phosphinous Acid Derivatives Containing t-Butyl Group as a Single Bulky Substituent: Synthetic, Mechanistic and Stereochemical Aspects

Drabowicz¹,

Kudelska²,

Łopusiński³

et al. 2007

COC

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Basic synthetic procedures commonly applied for the preparation of racemic and optically active phosphinic and phosphinous acid derivatives containing a t-butyl group as a single bulky substituent are presented. Mechanistic and stereochemical aspects of the presented protocols are discussed. Structural studies, which include the X-ray and vibrational circular dichroism-based determinations of the absolute configuration at the stereogenic phosphorus atom and calculations of conformational equilibria for a few model compounds are also mentioned. The use of the optically active tbutylphenylthiophosphinic acid as a chiral solvating agent is illustrated.

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Section: Synthesis and Reactions Of Halogenidesmentioning

confidence: 99%

Section: Synthesis and Reactions Of Halogenidesmentioning

confidence: 99%

Section: Synthesis and Reactions Of Halogenidesmentioning

confidence: 99%

See 1 more Smart Citation

The Chemistry of Phosphinic and Phosphinous Acid Derivatives Containing t-Butyl Group as a Single Bulky Substituent: Synthetic, Mechanistic and Stereochemical Aspects

Drabowicz¹,

Kudelska²,

Łopusiński³

et al. 2007

COC

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show abstract

“…The dynamic nature of the resolution allows high enantiomeric excesses to be obtained at full conversion. Previously, there have been very few reported successes of kinetic resolution (KR) or dynamic kinetic resolution (DKR) in such systems, [38][39][40] one of the few reported cases being that of Perlikowska et. al.…”

Section: Introductionmentioning

confidence: 99%

“…al. [38] who reported up to 39 % ee in the KR of P-stereogenic tertiary phosphanes and 70 % ee for a single example of the first DKR of a chlorophosphane. In our case, enantiomeric excesses of up to 82 % were achieved (Scheme 2) and some indications were obtained of the factors that influence the stereoselectivity of the reaction.…”

Section: Introductionmentioning

confidence: 99%