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Mukaiyama aldol addition to α-chloro-substituted aldehydes. Origin of the unexpected syn selectivity.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. (Peter Somfai)
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. (Peter Somfai)
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
2010 (engelsk)Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, nr 8, s. 1281-1283Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The addition of sterically demanding enolsilanes to alpha-chloro aldehydes results unexpectedly in preferential formation of the anti-PFA product (1,2-syn), while the addition of the corresponding boron enolate furnishes the expected polar Felkin-Anh product (1,2-anti). A stereoinduction model explaining these observations is proposed.

sted, utgiver, år, opplag, sider
2010. Vol. 46, nr 8, s. 1281-1283
Emneord [en]
ASYMMETRIC INDUCTION, 1, 3-ASYMMETRIC INDUCTION, ACYCLIC STEREOSELECTION, FELKIN-ANH, MODEL, ENOL, CONDENSATION, CORNFORTH, ENOLSILANES, GEOMETRY
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-50172DOI: 10.1039/b922954jISI: 000274396700028Scopus ID: 2-s2.0-76349096927OAI: oai:DiVA.org:kth-50172DiVA, id: diva2:461189
Tilgjengelig fra: 2011-12-02 Laget: 2011-12-02 Sist oppdatert: 2017-12-08bibliografisk kontrollert
Inngår i avhandling
1. Stereoselective Nucleophilic Additions to Aldehydes and Synthesis of α-Amino-β- Hydroxy-Esters
Åpne denne publikasjonen i ny fane eller vindu >>Stereoselective Nucleophilic Additions to Aldehydes and Synthesis of α-Amino-β- Hydroxy-Esters
2012 (engelsk)Licentiatavhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis deals with the development of new reaction methodology as well as stereochemical investigations.

The first part concerns the investigation of 1,2- and merged 1,2- and 1,3- asymmetric induction in Mukaiyama aldol additions to α-heteroatom and α,β- heteroatom substituted aldehydes respectively. In particular, the unexpected 1,2-syn selectivity obtained in the addition of sterically hindered nucleophiles to α-chloroaldehydes is examined, and an explanation for the observed stereochemical trends is proposed.

The second part describes the development of a novel entry to α-amino-β- hydroxy esters by a 1,3-dipolar cycloaddition reaction of aldehydes and azomethine ylides, generated by thermolysis of aziridines.

The third part deals with our efforts to develop a novel entry to vicinal all- carbon quaternary centers, based on an intramolecular domino Heck- carbonylation reaction using tetrasubstituted olefins.

sted, utgiver, år, opplag, sider
Stockholm: KTH Royal Institute of Technology, 2012. s. 60
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2012:32
Emneord
Asymmetric induction, stereochemical models, Mukaiyama, polar Felkin-Anh, Cornforth-Evans, 1, 3-dipole, aziridine, cycloaddition, amino alcohol, carbonylation, Heck reaction, quaternary stereocenter
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-95467 (URN)978-91-7501-396-1 (ISBN)
Presentation
2012-08-16, F3, KTH, Lindstedtsvägen 3, entréplan, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad
QC 20120611Tilgjengelig fra: 2012-06-11 Laget: 2012-05-25 Sist oppdatert: 2012-06-12bibliografisk kontrollert
2. Stereoselective Nucleophilic Additions to Aldehydes and Development of New Methodology in Organic Synthesis
Åpne denne publikasjonen i ny fane eller vindu >>Stereoselective Nucleophilic Additions to Aldehydes and Development of New Methodology in Organic Synthesis
2013 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: KTH Royal Institute of Technology, 2013. s. 62
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2013:8
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-121172 (URN)978-91-7501-690-0 (ISBN)
Disputas
2013-05-08, Kollegiesalen, Brinellvägen 8, KTH, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad

QC 20130503

Tilgjengelig fra: 2013-05-03 Laget: 2013-04-22 Sist oppdatert: 2013-05-03bibliografisk kontrollert

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