Literature DB >> 26236053

Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.

Nongnuch Sutivisedsak1, Surendra Dawadi1, Christopher D Spilling1.   

Abstract

Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.

Entities:  

Keywords:  Acetal; Allyl phosphonates; Catalysis; Cyclization; Palladium π-allyl; Vinyl phosphonates

Year:  2015        PMID： 26236053      PMCID： PMC4518476          DOI： 10.1016/j.tetlet.2015.01.050

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  18 in total

1.  Total synthesis of (2S,3S,5S,10S)-6,9-epoxynonadec-18-ene-7,10-diol and formal total synthesis of (+)-trans-kumausyne from D-arabinose.

Authors:  R R Gadikota; C S Callam; T L Lowary
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

2.  Using stereoelectronic effects to explain selective reactions of 4-substituted five-membered ring oxocarbenium ions.

Authors:  Deborah M Smith; K A Woerpel
Journal:  Org Lett       Date:  2004-06-10       Impact factor: 6.005

3.  The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride. The merged stereochemical impact of alpha- and beta-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles.

Authors:  D A Evans; B D Allison; M G Yang; C E Masse
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

4.  Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes.

Authors:  Scott E Denmark; Gregory L Beutner; Thomas Wynn; Martin D Eastgate
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

5.  Oxymercuration of homoallylic alcohol derived hemiacetals: diastereoselective synthesis of protected 1,3-diols.

Authors:  S T Sarraf; J L Leighton
Journal:  Org Lett       Date:  2000-02-10       Impact factor: 6.005

6.  Yb(OTf)(3)-Catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals.

Authors:  S D Dreher; K R Hornberger; S T Sarraf; J L Leighton
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

7.  First total synthesis of the antitumor compound (-)-kazusamycin A and absolute structure determination.

Authors:  Noriyoshi Arai; Noriko Chikaraishi; Satoshi Omura; Isao Kuwajima
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

8.  Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.

Authors:  Leticia Ayala; Claudia G Lucero; Jan Antoinette C Romero; Sarah A Tabacco; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-12-17       Impact factor: 15.419

9.  Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2010-10-28       Impact factor: 6.005

10.  Stereoselective synthesis of cyclic ethers via the palladium-catalyzed intramolecular addition of alcohols to phosphono allylic carbonates.

Authors:  Anyu He; Nongnuch Sutivisedsak; Christopher D Spilling
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.