A New Approach to the Synthesis of Primary Amines, Isothiocyanates, and 1-Aminoalkanephosphonates via<i>N</i>-Phosphinyl Aldoximes and Ketoximes

Krzyzanowska, B.; Stec, Wojciech J.

doi:10.1055/s-1978-24795

Cited by 67 publications

(26 citation statements)

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“…The aliphatic derivatives are not stable; as a rule, they are involved in the reaction without puri fication. The standard procedure for the removal of the Dpp fragment is acid solvolysis (a) on heating in concentrated HCl [60], (b) at ambient temperature in aqueous alcoholic solution of HCl [62,63], or (c) by treatment with gaseous HCl [61]. Yields vary from moderate to high.…”

Section: N Phosphinoyl Imines (Iii)mentioning

confidence: 99%

Stable synthetic equivalents of N-unsubstituted imines: Part 1. Synthesis

et al. 2012

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Section: N Phosphinoyl Imines (Iii)mentioning

confidence: 99%

Stable synthetic equivalents of N-unsubstituted imines: Part 1. Synthesis

et al. 2012

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“…The phosphinyl group is very attractive since its removal from the reduction products can be conveniently achieved under mild acidic conditions, leading to the free primary amines [22,23]. N-phosphinyl imines have found a variety of synthetic applications in asymmetric processes [10,24,25].…”

Section: Open Accessmentioning

confidence: 99%

Chiral β-Amino Alcohols as Ligands for the Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of N-Phosphinyl Ketimines

2012

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Some chiral β-amino alcohols have been evaluated as potential ligands for the ruthenium-catalyzed asymmetric transfer hydrogenation (ATH) of N-phosphinyl ketimines in isopropyl alcohol. The ruthenium complex prepared from [RuCl 2 (p-cymene)] 2 and (1S,2R)-1-amino-2-indanol has shown to be an efficient catalyst for the ATH of several N-(diphenylphosphinyl)imines, affording the reduction products in very good isolated yields and enantiomeric excesses up to 82%. The inherent rigidity of the indane ring system present in the ligand seems to be very important to achieve good enantioselectivities.

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“…[10] These derivatives are very commonly used and easily constructed, being obtained as a single (presumably E) isomer. Importantly, they can be readily hydrolyzed to the desired amines [10,11] without erosion of stereoechemical integrity in the newly formed product. Moreover, the nature of the phosphinyl residue was anticipated to be crucial in weakening an otherwise strong copper-nitrogen bond, the likely initial outcome from addition of the elements of CuÀH across the imine prior to any transmetalation event required for the regeneration of the metal catalyst (see compound 1, Scheme 2).…”

Section: Asymmetric Synthesismentioning

confidence: 99%

“…[21] The sense of chiral induction engendered by (R)-DTBM-SEGPHOS was determined for all substrates by treating each isolated product with HCl in alcoholic media. [11] Basic workup led to the respective primary amines for which the rotation of each was measured and compared with literature values. [22] In all cases, the (R)-amine was clearly formed.…”

Section: Asymmetric Synthesismentioning

confidence: 99%