- A novel approach to azasugars from vinyl glycine methyl ester via olefin metathesis
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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
- Huwe, Christoph M.,Blechert, Siegfried
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- Synthesis of vicinal aminoalcohols by stereoselective aza-wacker cyclizations: Access to (-)-acosamine by redox relay
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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
- Weinstein, Adam B.,Schuman, David P.,Tan, Zhi Xu,Stahl, Shannon S.
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p. 11867 - 11870
(2013/11/19)
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- An innovative strategy for the synthesis of a new series of potent aminopeptidase (APN or CD13) inhibitors derived from the oxepin-4-one family
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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
- Roux, Lionel,Charrier, Cédric,Salomon, Emmanuel,Ilhan, Meral,Bisseret, Philippe,Tarnus, Céline
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scheme or table
p. 2586 - 2589
(2011/06/21)
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- 2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated alkylating agents
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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
- Aponick, Aaron,Dietz, Amber L.,Pearson, William H.
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scheme or table
p. 4264 - 4276
(2009/04/11)
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- Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives
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(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.
- Sabat, Mark,Johnson, Carl R.
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p. 1089 - 1091
(2007/10/03)
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- The stereoselective synthesis of 2-substituted 3- azabicyclo[3.2.0]heptanes by intramolecular [2+2]-photocycloaddition reactions
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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
- Bach, Thorsten,Krueger, Christa,Harms, Klaus
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p. 305 - 320
(2007/10/03)
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- A flexible synthesis of azasugars and homoazasugars via olefin metathesis
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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
- Huwe, Christoph M.,Blechert, Siegfried
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- ASYMMETRIC CYCLIZATION OF 2-BUTENYLENE DICARBAMATES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEXES: CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE 2-AMINO-3-BUTENOLS
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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
- Hayashi, Tamio,Yamamoto, Akihiro,Ito, Yoshihiko
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