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Literature DB >> 16671771

Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

Abstract

[reaction: see text] The optically active gamma-hydroxy-alpha,beta-acetylenic esters are obtained from the enantioselective reaction of methyl propiolate with both aliphatic and aromatic aldehydes. These compounds can undergo regiospecific hydration in the presence of Zeise's dimer, [PtCl(2)(C(2)H(4))](2), to generate the optically active tetronic acids.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16671771 PMCID： PMC2597458 DOI： 10.1021/ol060377v

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

7 in total

1. Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Authors: Barry M Trost; Andrew H Weiss; Axel Jacobi von Wangelin
Journal: J Am Chem Soc Date: 2006-01-11 Impact factor: 15.419

2. Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters by asymmetric alkyne addition to aldehydes.

Authors: Ge Gao; Qin Wang; Xiao-Qi Yu; Ru-Gang Xie; Lin Pu
Journal: Angew Chem Int Ed Engl Date: 2005-12-16 Impact factor: 15.336

3. Synthetic stitching with silicon: geminal alkylation-hydroxylation of alkynyl carbonyl compounds.

Authors: Barry M Trost; Zachary T Ball
Journal: J Am Chem Soc Date: 2004-11-03 Impact factor: 15.419

4. Samarium(II) iodide-mediated intramolecular conjugate additions of alpha,beta-unsaturated lactones.

Authors: Gary A Molander; David J St Jean
Journal: J Org Chem Date: 2002-05-31 Impact factor: 4.354

5. Efficient domino process based on the catalytic generation of non-metalated, conjugated acetylides in the presence of aldehydes or activated ketones.

Authors: David Tejedor; Fernando García-Tellado; José Juan Marrero-Tellado; Pedro de Armas
Journal: Chemistry Date: 2003-07-07 Impact factor: 5.236

6. 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity.

Authors: B E Roggo; F Petersen; R Delmendo; H B Jenny; H H Peter; J Roesel
Journal: J Antibiot (Tokyo) Date: 1994-02 Impact factor: 2.649

7. Trans-selective conversions of gamma-hydroxy-alpha,beta-alkynoic esters to gamma-hydroxy-alpha,beta-alkenoic esters.

Authors: Christopher T Meta; Kazunori Koide
Journal: Org Lett Date: 2004-05-27 Impact factor: 6.005

7 in total

5 in total

Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

1. Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

2. Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters by asymmetric alkyne addition to aldehydes.

3. Synthetic stitching with silicon: geminal alkylation-hydroxylation of alkynyl carbonyl compounds.

4. Samarium(II) iodide-mediated intramolecular conjugate additions of alpha,beta-unsaturated lactones.

5. Efficient domino process based on the catalytic generation of non-metalated, conjugated acetylides in the presence of aldehydes or activated ketones.

6. 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity.

7. Trans-selective conversions of gamma-hydroxy-alpha,beta-alkynoic esters to gamma-hydroxy-alpha,beta-alkenoic esters.

1. The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

2. Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D.

3. Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

4. Total synthesis and stereochemical assignment of (-)-ushikulide A.

Review 5. Asymmetric functional organozinc additions to aldehydes catalyzed by 1,1'-bi-2-naphthols (BINOLs).