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- W2624414916 abstract "Tetra-tert-butyl-P5-deltacyclene 5 represents one of only two asymmetric P-C cage compounds, which are available in highly enantiomerically enriched versions. This paper reports about stereoselective substitution reactions of 5 to develop the chemistry of optically active P-C cages further. Electrophilic substitution of the only secondary phosphorus atom P1 of the cage with methyl and benzyl groups was achieved with 92 % and >99 % de, but the yields of the reactions are limited due to competing processes. The uncatalyzed hydrophosphination reaction of a monosubstituted allene and two α,β-unsaturated carbonyl compounds with 5 proved to be the method of choice. cis-Butanone-P5-deltacyclene 12 is formed in 92 % yield and with >99 % de and cis-pentanone-P5-deltacyclene 13a is accessible with >99 % de for P1 and 92 % de for the attached carbon atom at the same time. Besides stereoselectivity, the hydrophosphination reaction of 5 performs with a good regioselectivity. The chiral cage 5 controls the stereoselectivity of its reactions for the cage elements as well as for the α position of a substituent." @default.
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- W2624414916 date "2017-06-07" @default.
- W2624414916 modified "2023-09-24" @default.
- W2624414916 title "Stereoselective P5-Deltacyclene Alkylation, an Efficient Route to New Asymmetric P-C-Cage Compounds" @default.
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- W2624414916 doi "https://doi.org/10.1002/zaac.201700132" @default.
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