Phosphororganische verbindungen XLII darstellung eines optisch aktiven triarylphosphins

Horner, L.; Schedlbauer, F.; Beck, P.

doi:10.1016/s0040-4039(00)90492-1

Cited by 15 publications

(4 citation statements)

References 1 publication

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“…In the meantime, however, in 1967 Wittig et al71 partially resolved a triarylphosphine via kinetic resolution (cf. section III.A.4), and in 1968 Chan,72 by adapting the method developed by Cope for resolution of strained olefins and sulfoxides,73 succeeded in partially resolving tert-butylmethylphenylphosphine (31) through its diastereomeric platinum(II) complexes with (+)-deoxyephedrine (eq 7). The tert-butylmethylphenylphosphine oxide obtained by in situ oxidation of the liberated phosphine was of ca.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Scalemic P-Chiral Phosphines and Their Derivatives

Pietrusiewicz¹,

Zabłocka²

1994

Chem. Rev.

627

276

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Section: Introductionmentioning

confidence: 99%

Preparation of Scalemic P-Chiral Phosphines and Their Derivatives

Pietrusiewicz¹,

Zabłocka²

1994

Chem. Rev.

627

276

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“…This mechanistic interpretation requires that optically active lb must lead to optically active 4b with retained or inverted configuration.9 Similarly, 4 cannot be derived from diradical 3, since decarboxylation with concurrent cyclization must give optically active 4b from active lb. Thus, the stereochemical results demand that the 1-oxatrimethylene diradical 2 serves as a precursor to epoxide 4 and that diradical 2 is sufficiently long-lived to racemize completely before cyclization into 4 takes place. Furthermore, fragmentation into ketone 5 and rearrangement into ketones 6 and 7 compete with cyclization (Table I) and, as expected, racemic 7b is formed in the photolysis of (S)-(-)-lb since racemized diradical 2b is the precursor to the photoproducts.…”

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confidence: 99%

“…Treatment with bis(diphenylphosphino)ethane of 4 and 5 provided optically active a-naphthylphenyl-otolylphosphine, [<x]26d -1.04°( c 7.72, CH2C12) and -naphthylphenyl-p-ethoxyphenylphosphinej…”

mentioning

confidence: 99%

Partial resolution of racemic tertiary phosphines with an asymmetric palladium complex

Otsuka¹,

Nakamura²,

Kano³

et al. 1971

J. Am. Chem. Soc.

113

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Optically active tertiary phosphines can serve as key ligands in the transition metal catalyzed asymmetric hydrogenation of olefins.1•2 They have been prepared through asymmetric syntheses3-5 or by resolution of racemates,6•7 most of which require tedious steps.Here we propose a simple method of resolving racemic tertiary phosphines through stereospecific reactions of an asymmetric palladium(II) complex.

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“…The present revival of interest in phosphorus stereochemistry perhaps began with the resolution of phosphonium salts I and II (3, 4)-A number of earlier workers had attempted the resolution of phosphonium salts but all met with failure (5)(6)(7)(8)(9)(10)(11)(12)(13), apparently as a result of the inherent difficulties in crystallizing these compounds (4). The first optically active quaternary phosphorus compound obtained, in which the phosphorus atom was not incorporated in a heterocyclic ring, was resolved via its dibenzoylhydrogen-tartarate salt (14)-A number of phosphonium salts have been resolved since then by the same method (15)(16)(17). The absolute configuration of one of these salts, {+)-benzyImethylphenyl-n-propylphosphonium bromide, III, has recently been determined (18).…”

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confidence: 99%