94944-69-1Relevant articles and documents
Preparation methods and applications of chiral spirophosphine-nitrogen-phosphine tridentate ligand and iridium catalyst thereof
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Paragraph 0265-0273, (2020/08/18)
The invention relates to preparation methods and applications of a chiral spirophosphine-nitrogen-phosphine tridentate ligand SpiroPNP and an iridium catalyst Ir-SpiroPNP thereof. The chiral spirophosphine-nitrogen-phosphine tridentate ligand is a compound represented by a formula I, or a racemate or an optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly structurallycharacterized by having a chiral spiro indane skeleton and a phosphine ligand with a large steric hindrance substituent. The chiral spirophosphine-nitrogen-phosphine tridentate ligand can be synthesized by taking a 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro indane compound with a spiro skeleton as a chiral starting raw material. The iridium catalyst of the chiral spirophosphine-nitrogen-phosphinetridentate ligand is a compound represented by a formula II which is described in the specification, or a raceme or an optical isomer, or a catalytically acceptable salt thereof, can be used for catalyzing asymmetric catalytic hydrogenation reaction of carbonyl compounds, particularly shows high yield (greater than 99%) and enantioselectivity (as high as 99.8% ee) in asymmetric hydrogenation reaction of simple dialkyl ketone, and has practical value.
Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone
McLaughlin, Noel P.,Evans, Paul
scheme or table, p. 518 - 521 (2010/03/30)
(Chemical Equation Presented) The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.
Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.
Huh, Nam,Thompson, Charles M.
, p. 5935 - 5950 (2007/10/02)
The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.