146937-36-2Relevant academic research and scientific papers
Asymmetric synthesis of syn- and anti-α-deuterio-β3- phenylalanine derivatives
Davies, Stephen G.,Foster, Emma M.,McIntosh, Catherine R.,Roberts, Paul M.,Rosser, Timothy E.,Smith, Andrew D.,Thomson, James E.
experimental part, p. 1035 - 1050 (2011/10/04)
The conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl) amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium β-amino enolates with D2O provides access to anti configured α-deut
Chemoselective oxidative debenzylation of tertiary N-benzyl amines
Bull, Steven D.,Davies, Stephen G.,Fenton, Garry,Mulvaney, Andrew W.,Prasad, R. Shyam,Smith, Andrew D.
, p. 337 - 338 (2007/10/03)
Treatment of tertiary amines containing one or more N-benzyl protecting groups with aqueous ceric ammonium nitrate results in clean N-debenzylation to afford the corresponding secondary amine.
Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate
Bull, Steven D.,Davies, Stephen G.,Fenton, Carry,Mulvaney, Andrew W.,Shyam Prasad,Smith, Andrew D.
, p. 3765 - 3774 (2007/10/03)
Treatment of a range of N-benzyl tertiary amines with aqueous eerie ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-W-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and 5-benzyl ethers. The Royal Society of Chemistry 2000.
Asymmetric synthesis of homochiral Baylis-Hillman products employing (R)-N-methyl-N-α-methylbenzyl amide
Davies, Stephen G.,Smethurst, Christian A.P.,Smith, Andrew D.,Smyth, G. Darren
, p. 2437 - 2441 (2007/10/03)
The conjugate addition of (R)-N-methyl-N-α-methylbenzyl amide to tert-butyl cinnamate followed by an asymmetric aldol reaction and subsequent N-oxidation/Cope elimination affords β-substituted homochiral Baylis-Hillman products in good yield. Copyright (C
Synthesis of β-amino esters by the conjugate addition of nitrogen nucleophiles to α,β-unsaturated esters having chiral p-tolylsulfinyl groups
Matsuyama, Haruo,Itoh, Nobuhiro,Yoshida, Masato,Kamigata, Nobumasa,Sasaki, Sigeru,Iyoda, Masahiko
, p. 375 - 376 (2007/10/03)
The conjugate addition of nitrogen nucleophiles to t-butyl (E)-2-(p-tolylsulfinyl)cinnamates (1) afforded the corresponding chiral β-amino esters, which are important building blocks for synthesis of biologically active polyamine alkaloids. The diastereos
Lithium (α-Methylbenzyl)allylamide: A Differentially Protected Chiral Ammonia Equivalent for the Asymmetric Synthesis of β-Amino Acids and β-Lactams
Davies, Stephen G.,Fenwick, David R.
, p. 1109 - 1110 (2007/10/02)
The addition products from the highly stereoselective conjugate additions of lithium (αS)-(α-methylbenzyl)allylamide to α,β-unsaturated tert-butyl esters are efficiently deallylated with tris(triphenylphosphine)rhodium(I) chloride and converted, after tra
A new chiral BLA promoter for asymmetric aza Diels - Alder and aldol-type reactions of imines
Ishihara, Kazuaki,Miyata, Mayumi,Hattoi, Kouji,Tada, Toshiji,Yamamoto, Hisashi
, p. 10520 - 10524 (2007/10/02)
A new type of chiral promoter for double asymmetric inductions of aza Diels - Alder and aldol-type reactions of imines is prepared from trialkyl borates (B(OMe)3 or B(OPh)3) and optically pure binaphthol; X-ray analysis of the boron complex demonstrates that it exists as a Br?nsted acid-assisted chiral Lewis acid (BLA). The aldol-type reactions of a number of N-benzhydrylimines derived from aromatic aldehydes with the ketene silyl acetal derived from tert-butyl acetate mediated by the chiral BLA afford β-amino acid esters with high enantioselectivity. The solution conformations of the BLA·imine complexes have been studied using 1H NMR analysis and difference NOE measurements. The absolute configurations of the adducts can be understood in terms of a rational model involving an intramolecular hydrogen binding interaction via a Br?nsted acid.
