213887-77-5Relevant academic research and scientific papers
Chiral tetraaminophosphonium salt-mediated asymmetric direct henry reaction
Uraguchi, Daisuke,Sakaki, Sawako,Ooi, Takashi
, p. 12392 - 12393 (2007)
Chiral tetraaminophosphonium salts 1 possessing the phosphorus-centered [5.5]-spirocyclic core have been designed and synthesized in a single step from l-valine-derived diamine. The three-dimensional molecular structure was successfully verified by the si
Ethynylbenziodoxolones (EBX) as reagents for the ethynylation of stabilized enolates
Fernandez Gonzalez, Davinia,Brand, Jonathan P.,Mondiere, Regis,Waser, Jerome
, p. 1631 - 1639 (2013/07/05)
Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scannin
CHIRAL TETRAAMINOPHOSPHONIUM SALTS, CATALYST FOR ASYMMETRIC SYNTHESIS AND METHOD FOR PRODUCING CHIRAL beta-NITROALCOHOL
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Page/Page column 7, (2009/05/28)
A chiral tetraaminophosphonium salt represented by formula (1) and a method for producing chiral β-nitroalcohol comprising reacting an aldehyde or a ketone and a nitroalkane in the presence of the chiral tetraaminophosphonium salt represented by formula (
Highly effective and recyclable chiral auxiliaries: A study of the synthesis and use of three 4-isopropyl-5,5-diaryloxazolidin-2-ones
Alexander,Cook,Gibson,Kennedy
, p. 1538 - 1549 (2007/10/03)
A series of three 5,5-diaryl substituted oxazolidin-2-ones (diphenyl, dinaphthyl and ditolyl) have been synthesised. Studies on the benzylation of the lithium enolates of N-acyl derivatives reveal that the yields obtained were sensitive to the method of quenching the reaction. This was particularly acute for the 5,5-diphenyl system where effective yields (69%) and high diastereoselectivities (dr 98 : 2) are only observed when the reactions were quenched into aqueous buffer. Methylation studies on the N-acyl derivatives showed that the most advantageous results (58-69%, dr ≥ 91 : 9) were only observed using the sodium enolates. The 5,5-ditolyl-4-isopropyloxazolidin-2-one proved to be more efficacious in terms of efficiency and diastereoselectivity (dr ≥ 97 : 3). Subsequent, simple alkaline hydrolyses of the alkylation products allowed for the high recovery and recyclability of the 5,5-diaryl substituted oxazolidin-2-ones without any deleterious endocyclic cleavage. In addition, the acyl portions were recovered in high yield from the alkaline hydrolyses without any evidence of racemisation.
A study of 4-substituted 5,5-diaryl oxazolidin-2-ones as efficacious chiral auxiliaries
Gibson, Colin L.,Gillon, Karen,Cook, Stuart
, p. 6733 - 6736 (2007/10/03)
A series of three 5,5-diaryl substituted oxazolidin-2-ones (diphenyl, dinaphthyl and ditolyl) have been prepared and shown to be particularly effective chiral auxiliaries to afford high yields and diastereoselectivities for alkylation and azidations of their N-acyl derivatives. The 5,5-ditolyl oxazolidin-2-one proved to be particularly efficacious in terms of diastereoselectivity, yield and solubility.
