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- W2090102434 abstract "Abstract Asymmetric reactions on chiral bis (diphenylphosphine) metal complexes having C2 symmetry axis of the chelate ring obey the simple stereochemical rules which establish a relationship between the product configuration and complex conformation. The stereochemical basis of the application of this rule has been studied on the example of the cross-coupling reaction of crotyl alcohol derivatives and arylmegnesiumbromides on trans-bis-1S,2S- and trans-bis-1R,2R- (diphenylphosphino)cyclopentanenickel dibromide (NiBr2 ((SS)-dpcp) and NiBr2 ((RR)-dpcp)). Monitoring the reaction mixture by circular dichroism and 31P NMR spectroscopy shows that this reaction goes through Ni(Ph)Br(dpcp), NiPh2(dpcp) and Ni0(dpcp) intermediates. 31P NMR spectroscopy, just as CD, did not reveal the π-allyl (Y)Ni(dpcp) species (Y = leaving group of the crotyls). Probably, they take part in the reaction at a very small concentration. The observed effect of the influence of Y volume on the enantiomeric excess value of the reation was explained on the assumption of an equilibrium between two forms: in the one, the Ni in Ni(Y) (dpcp) is coordinated to the crotyl function, and in the other, Y is covalently bonded to the crotyl, with the Ni π-bonded to the crotyl double bond. Exchange of phenyl for 1-naphthyl group in ArMgBr is accompanied by a decrease of ee from 58% to 0%. Loss of enantioselectivity can be explained by attack of the bulky nucleophile from outside but not within the inner sphere of the complex as in the case of Ph. Major and minor diastereomers (8:1) of π-allyl(1-Np)Ni((SS)-dpcp) are not intermediates of this reaction but deadlock substances." @default.
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- W2090102434 date "1993-02-01" @default.
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- W2090102434 title "Stereochemistry in cross-coupling reaction of crotyl alcohol derivatives and arylmagnesium bromides on trans-bis-1S, 2S- and trans-bis-1R,2R- (diphenylphosphino) cyclopentanenickel dibromide" @default.
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- W2090102434 doi "https://doi.org/10.1016/0304-5102(93)85091-7" @default.
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