186759-45-5Relevant academic research and scientific papers
A novel approach to azasugars from vinyl glycine methyl ester via olefin metathesis
Huwe, Christoph M.,Blechert, Siegfried
, p. 1621 - 1624 (1995)
A novel strategy for the synthesis of azasugars from vinyl glycine methyl ester was designed, using an olefin metathesis as a key step. As a first test of this strategy, rac-trans-2-hydroxymethyl-3-hydroxypyrrolidine, which was isolated as the (2R,3S)-iso
Synthesis of vicinal aminoalcohols by stereoselective aza-wacker cyclizations: Access to (-)-acosamine by redox relay
Weinstein, Adam B.,Schuman, David P.,Tan, Zhi Xu,Stahl, Shannon S.
, p. 11867 - 11870 (2013/11/19)
Diastereoselective aza-Wacker cyclization of O-allyl hemiaminals under aerobic conditions enables efficient access to 1,2-aminoalcohol derivatives from allylic alcohols. The scope of this method is presented and its utility is highlighted in a streamlined
An innovative strategy for the synthesis of a new series of potent aminopeptidase (APN or CD13) inhibitors derived from the oxepin-4-one family
Roux, Lionel,Charrier, Cédric,Salomon, Emmanuel,Ilhan, Meral,Bisseret, Philippe,Tarnus, Céline
scheme or table, p. 2586 - 2589 (2011/06/21)
Derivatives from the aminobenzosuberone family have been recently synthesized and recognized as highly selective inhibitors of aminopeptidase N (APN)/CD13 (EC 3.4.11.2), an important target for cell migration processes involved in particular in tumor inva
2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated alkylating agents
Aponick, Aaron,Dietz, Amber L.,Pearson, William H.
scheme or table, p. 4264 - 4276 (2009/04/11)
The preparation of 2-(3-pyrrolin-1-yl)-1,4-naphthoquinones and a study of their use as photoactivated alkylating agents is reported. The title compounds were easily synthesized by conjugate addition of the corresponding 3-pyrrolines to various naphthoquin
The stereoselective synthesis of 2-substituted 3- azabicyclo[3.2.0]heptanes by intramolecular [2+2]-photocycloaddition reactions
Bach, Thorsten,Krueger, Christa,Harms, Klaus
, p. 305 - 320 (2007/10/03)
The stereoselective synthesis of the 3-azabicyclo[3.2.0]heptanes 6, 12, 13, 17, 22, 23 and 24 by an intramolecular [2+2]-photocycloaddition is described. The product yield was good to excellent in almost all cases studied (65-87%) except for a single exam
Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives
Sabat, Mark,Johnson, Carl R.
, p. 1089 - 1091 (2007/10/03)
(R and S)-α-Amino alcohols and α-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant α-amino alcohols are described.
A flexible synthesis of azasugars and homoazasugars via olefin metathesis
Huwe, Christoph M.,Blechert, Siegfried
, p. 61 - 67 (2007/10/03)
A flexible synthesis of azasugars and homoazasugars from vinyl glycine methyl ester is described. The syntheses, which are based on ring closing olefin metathesis steps and stereocontrolled functionalizations of the formed double bonds, offer a broad vari
ASYMMETRIC CYCLIZATION OF 2-BUTENYLENE DICARBAMATES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEXES: CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE 2-AMINO-3-BUTENOLS
Hayashi, Tamio,Yamamoto, Akihiro,Ito, Yoshihiko
, p. 99 - 102 (2007/10/02)
Cyclization of 2-butenylene dicarbamates (RNHCOOCH2CH=CHCH2OCONHR: R = Ph, MeOC6H4, PhCH=CH, etc.) in the presence of a palladium catalyst coordinated with chiral (hydroxyalkyl)-ferrocenylphosphine ligand gave optically active 4-vinyl-2-oxazolidines (up t
