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Synthesis 2020; 52(06): 909-916
DOI: 10.1055/s-0039-1691531
DOI: 10.1055/s-0039-1691531
paper
Enantiodivergent Synthesis of Both PAMPO Enantiomers Using l-Menthyl Chloroacetate and Stereomutation at P in Classical Quaternisation Reactions
We thank Narodowe Centrum Nauki (National Science Centre, Poland) for partly funding this work through grant NN204 265 238.Weitere Informationen
Publikationsverlauf
Received: 08. Oktober 2019
Accepted after revision: 19. November 2019
Publikationsdatum:
04. Dezember 2019 (online)

Abstract
A practical protocol for efficient synthesis of both PAMPO enantiomers as well as related functionalised P-stereogenic phosphine oxides in 1–3 steps from effectively resolved (S P)-l-menthyl o-anisyl-(phenyl)phosphinylacetate has been developed. Examples of non-stereoselective quaternisation of a tertiary phosphine by alkyl halides have been revealed.
Key words
P-stereogenic phosphine oxides - PAMPO - resolution - phosphines - pyramidal inversion - non-stereoselective quaternisationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691531.
- Supporting Information
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See also:
Also, for unprecedented clean inversion of configuration at P observed in an intramolecular SN2 reaction involving a secondary phosphine as nucleophile, see: