Enantiodivergent Synthesis of Both PAMPO Enantiomers Using L-Menthyl Chloroacetate and Stereomutation at P in Classical Quaternisation Reactions

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-stereo-selective quaternisation of a...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 52; no. 6; pp. 909 - 916
Main Authors Dziuba, Kamil, Lubanska, Malgorzata, Pietrusiewicz, K. Michal
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.03.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
P-stereogenic phosphine oxides
phosphines
PHOSPHORUS
RHODIUM
SECONDARY
TERTIARY PHOSPHINE OXIDES
INVERSION
resolution
non-stereoselective quaternisation
pyramidal inversion
ABSOLUTE-CONFIGURATION
REDUCTION
ASYMMETRIC HYDROGENATION
STEREOSELECTIVE-SYNTHESIS
PAMPO
DISPLACEMENT ROUTE
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Summary: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-stereo-selective quaternisation of a tertiary phosphine by alkyl halides have been revealed.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0039-1691531