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Lewis Acid-Promoted Addition of 1,3-Bis(silyl)propenes to Aldehydes: A Route to 1,3-Dienes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2011 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 19, 8070-8075 p.Article in journal (Refereed) Published
Abstract [en]

The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.

Place, publisher, year, edition, pages
2011. Vol. 76, no 19, 8070-8075 p.
Keyword [en]
diels-alder reaction, olefination reaction, wittig olefination, conjugated dienes, stereochemistry, allylsilanes, elimination, mechanism, oxidation, alcohols
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-46847DOI: 10.1021/jo2013466ISI: 000295302300049Scopus ID: 2-s2.0-80054119264OAI: oai:DiVA.org:kth-46847DiVA: diva2:454387
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note
QC 20111107Available from: 2011-11-07 Created: 2011-11-07 Last updated: 2017-12-08Bibliographically approved
In thesis
1. Stereoselective Nucleophilic Additions to Aldehydes and Development of New Methodology in Organic Synthesis
Open this publication in new window or tab >>Stereoselective Nucleophilic Additions to Aldehydes and Development of New Methodology in Organic Synthesis
2013 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is divided into four separate parts with nucleophilic addition to aldehydes as the common feature in three of them.

The first part deals with the investigation of the stereochemical induction and elucidation of the factors that dictate the p-facial selectivities in Mukaiyama aldol addition to a- and a,b-heteroatom substituted aldehydes. An explanation for the unexpected shift from 1,2-anti to 1,2-syn selectivity seen in the reaction when applying nucleophiles of different sizes in the addition to a-chloro aldehydes is offered.

The next two parts describes the addition of 1,3-bis(silyl)propenes and C3 substituted 1,3-bis(silyl)propenes to aldehydes and the development of two highly stereoselective new methodologies for the construction of 1,3-dienes and 2,3,4,5-tetrasubstituted tetrahydrofuranes, respectively.

The last part describes the attempts made towards the total synthesis of (±)-aspidophylline A, where the intention was to apply a domino carbopalladation-carbonylation reaction as the key step in the synthetic route.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2013. 62 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2013:8
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-121172 (URN)978-91-7501-690-0 (ISBN)
Public defence
2013-05-08, Kollegiesalen, Brinellvägen 8, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20130503

Available from: 2013-05-03 Created: 2013-04-22 Last updated: 2013-05-03Bibliographically approved

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