Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols.

Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Research Abstract Details 

Research Abstract Table of Contents

Jump to the:

Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Abstract Text:

Sharon A Powell,Jason M Tenenbaum,K A Woerpel,

We have developed a route for the stereoselective synthesis of 1-oxa-2,2-(dimesityl)silacyclopentane acetals, intermediates in the synthesis of highly functionalized 1,3-diols. This route involves a diastereoselective conjugate addition reaction of a hydrosilyl anion, a subsequent diastereoselective enolate alkylation, and a fluoride-catalyzed intramolecular hydrosilylation reaction to afford the oxasilacyclopentane acetal. A highly selective nucleophilic substitution reaction, followed by oxidation of the C-Si bond, leads to the desired polyol.

Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Publishing Authors By Initials

SA Powell,JM Tenenbaum,KA Woerpel,

For similar inorganic chemicals: silicon compounds: silanes research abstracts see: inorganic chemicals: silicon compounds: silanes research

PUBMED ID PMID:

MEDLINE DATE:

Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 124

Page Numbers: 12648-9

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 30

MONTH: Oct

YEAR: 2002

Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Keywords Mesh Terms:

KEYWORDS: Silanes

MESH TERMS: chemistry

Chemical & Substance for Abstract: Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols. Information

Substance Name: Silanes

Registry Number: 0

Grant and Affiliation Information for Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols.

AFFILIATION: Department of Chemistry, University of California, Irvine 92697-2025, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM54909

ACRONYM: GM

MEDLINETA: J Am Chem Soc

REFSOURCE:

DATABASENAME:

ACCESSION NUMBER:

Number Hits: 0

Utilization of 1-oxa-2,2-dimesitylsilacyclopentane acetals in the stereoselective synthesis of polyols Related Publications

• C-Glycosylation Reactions of Sulfur-Substituted Glycosyl Donors: Evidence against the Role of Neighboring-Group Participation.
• Dearomatization reactions of aryl-substituted silaaziridines.
• Diastereoselective silacyclopropanations of functionalized chiral alkenes.
• Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions.
• Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols.
• Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.
• Formation of chiral quaternary carbon stereocenters using silylene transfer reactions: enantioselective synthesis of (+)-5-epi-acetomycin.
• Metal-catalyzed silylene insertions of allylic ethers: stereoselective formation of chiral allylic silanes.
• Metal-catalyzed silylene transfer to imines: synthesis and reactivity of silaaziridines.
• Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control.
• Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: an analysis of the factors controlling stereoselectivity.
• Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters.
• Structural evidence that alkoxy substituents adopt electronically preferred pseudoaxial orientations in six-membered ring dioxocarbenium ions.
• Synthesis of (+/-)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates.
• Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters.
• Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols.
• [3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.