By Jean-Luc Montchamp

ISBN-10: 3319155113

ISBN-13: 9783319155111

ISBN-10: 3319155121

ISBN-13: 9783319155128

Each evaluation in the quantity severely surveys one point of that subject and areas it in the context of the quantity as a complete. the main major advancements of the final five to ten years are offered utilizing chosen examples to demonstrate the rules mentioned. The assurance isn't really meant to be an exhaustive precis of the sector or comprise huge amounts of knowledge, yet should still otherwise be conceptual, targeting the methodological pondering that might permit the non-specialist reader to appreciate the data provided. Contributions additionally supply an outlook on strength destiny advancements within the field.

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The asymmetric hydrogenation of cyclic enamides 146 was also performed (Scheme 52, (2)). 2% ee CO2H NH2 Me HO 150 Scheme 53 Asymmetric hydrogenation toward (S)-20 ,60 -dimethyltyrosine 150, a non-natural amino acid building blocks present in several important pharmaceuticals. 2%) using Rh-Quinox complex (Scheme 53). Optically pure tert-butylmethylphosphine-borane (17d) was also used by the group of Imamoto to produce novel palladium-P-stereogenic P–C–P pincers, which were successfully applied in the asymmetric addition of diarylphosphines to nitroalkenes [93].

The reaction of {(Me3Si)2CH}(Ph)PH (173) with 1 equiv. of BH3•SMe2 led to the formation of the phosphine-borane complex 174, which was subsequently deprotonated with 1 equiv. of n-BuLi to give rise to the lithium complex [[{(Me3Si)2CH}(Ph)P(BH3)]Li(THF)2]1 (175). Single-crystal X-ray structure of the lithium phosphido-borane complex shows that it crystallizes as infinite chains of alternating lithium cations and phosphido-borane anions. Each lithium cation was found to be coordinated to the phosphorus atom of each phosphido-borane, and also to the two boron hydrides (η2-manner).

Full racemization was observed with optically active substrates 98, probably because of the nucleophilicity of the chloride counterion of 97. Indeed, switching from chlorophosphonium to alkoxyphosphonium salts 99 as intermediates by using methyl triflate or Meerwein’s type salts as alkylating agents allowed the reaction to proceed stereospecifically with inversion of configuration (Scheme 38, (2)). ) diglyme reflux, 2 h R = Me, Et X = OTf or BF4 BH3 P 1 (2) Ph R Me 100 6 examples 67-76% retention of stereopurity Scheme 38 One-pot conversion of phosphine oxides or sulphides into phosphine-boranes using NaBH4 and an alkylating reagent related well-known Imamoto’s procedure [79], NaBH4 is unable to reduce phosphine oxides directly, and this inert character may also account for the clean retention of stereopurity.

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Phosphorus Chemistry II: Synthetic Methods by Jean-Luc Montchamp


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