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Simple, Enantiocontrolled Synthesis of 3-Pyrrolines from α-Amino Allenes
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2004 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2004, no 15, 3240-3243 p.Article in journal (Refereed) Published
Abstract [en]

Cyclization of -amino allenes in the presence of N-bromosuccinimide afforded pyrrolines in good yields. The products were obtained with high enantiomeric excesses when optically active allenes were used as substrates. The synthesis of a 2,5-dehydroprolinol derivative is also presented.

Place, publisher, year, edition, pages
wiley , 2004. Vol. 2004, no 15, 3240-3243 p.
Keyword [en]
Allenes;Cyclization;Nitrogen heterocycles
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-24400DOI: 10.1002/ejoc.200400211OAI: oai:DiVA.org:su-24400DiVA: diva2:197447
Note
Part of urn:nbn:se:su:diva-70Available from: 2004-03-11 Created: 2004-03-11 Last updated: 2010-10-21Bibliographically approved
In thesis
1. Palladium(II)-Catalyzed Reactions of Allenes with Lithium Bromide and Cyclization of α-Amino Allenes to Pyrrolines
Open this publication in new window or tab >>Palladium(II)-Catalyzed Reactions of Allenes with Lithium Bromide and Cyclization of α-Amino Allenes to Pyrrolines
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is based on three novel palladium(II)-catalyzed reactions of allenes with lithium bromide and a bromonium ion induced cyclization of allenyl amides to pyrrolines. In Paper I a 1,2-functionalization of allenes is presented where bromide adds as a first nucleophile followed by intramolecular attack by an oxygen or nitrogen nucleophile. Chapter 2 deals with the extension of this reaction to different nitrogen nucleophiles such as urea, carbamate, and N-tosyl carbamate providing access to substituted pyrrolidines and oxazolidines in good yields under mild reaction conditions.

Paper II deals with a stereoconvergent, palladium(II)-catalyzed SN2’ reaction of α-acetoxy allenes with bromide as nucleophile. In this reaction substituted (Z,E)-2-bromo-1,3-dienes are produced in good yields with excellent diastereo-selectivity.

Paper III describes a mild racemization reaction of chiral allenes. The effect of the functional group present in the molecule on the reaction rate is examined. All these reactions published in Papers I-III proceed through a common intermediate: a 2-bromo-(π-allyl)palladium complex.

The fourth paper describes a simple, efficient, and enantiocontrolled cyclization of N-protected α-allenyl amines with N-bromosuccinimide (NBS) to afford 3-bromo-pyrrolines. The synthesis of optically active 2,5-dehydroprolinol derivative is also described. The mechanism, scope, and limitations of all four reactions are discussed in this thesis.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2004. 44 p.
Keyword
Palladium, allene, pyrroline, palladium(II)-catalysis
Identifiers
urn:nbn:se:su:diva-70 (URN)91-7265-820-7 (ISBN)
Public defence
2004-03-31, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved

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