| 1. |
- Lindström, Ulf M., et al.
(författare)
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Microwave-assisted aminolysis of vinylepoxides
- 1999
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Ingår i: Tetrahedron Letters. - 0040-4039 .- 1359-8562. ; 40:52, s. 9273-9276
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Tidskriftsartikel (refereegranskat)abstract
- Di- and trisubstituted vinyl epoxides in NH4OH were subjected to microwave irradn. affording the corresponding vicinal amino alcs. in high yields. The reaction is stereospecific and highly regioselective for addn. at the allylic carbon. [on SciFinder(R)]
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| 2. |
- Olofsson, Berit, et al.
(författare)
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A regio- and stereodivergent route to all isomers of vic-amino alcohols
- 2002
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 67:24, s. 8574-8583
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Tidskriftsartikel (refereegranskat)abstract
- Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.
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| 3. |
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| 4. |
- Olofsson, Berit, et al.
(författare)
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A regio- and stereodivergent synthesis of vic-amino alcohols
- 2000
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Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 2:25, s. 4087-4089
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Tidskriftsartikel (refereegranskat)abstract
- [GRAPHICS] A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.
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| 5. |
- Olofsson, Berit, et al.
(författare)
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Determination of the relative configuration of vic-amino alcohols
- 2003
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Ingår i: Tetrahedron Letters. - 0040-4039 .- 1359-8562. ; 44:6, s. 1279-1281
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Tidskriftsartikel (refereegranskat)abstract
- A large set of syn- and anti-1,2-amino alcohols has been synthesized. Upon comparison of the CHO and CHN H-1 NMR shifts a general trend has been observed, making it possible to determine the relative configuration of 1,2-amino alcohols without derivatization or shift reagents.
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| 6. |
- Olofsson, Berit, et al.
(författare)
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Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers
- 2003
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 68:6, s. 2514-2517
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Tidskriftsartikel (refereegranskat)abstract
- Starting from a vinyl epoxide, a divergent synthesis of four sphingosine isomers is described. The remaining four isomers can easily be synthesized using the same methodology. Although numerous syntheses of sphingosine have been published, this is the first general route leading to all eight isomers in this important compound class. The synthetic strategy relies on regioselective opening of a vinyl epoxide and a vinylaziridine in the allylic position.
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| 7. |
- Olofsson, Berit, et al.
(författare)
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Synthesis of N-H vinylaziridines : a comparative study
- 2002
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Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 58:30, s. 5979-5982
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Tidskriftsartikel (refereegranskat)abstract
- Vinylaziridines are useful and versatile synthetic intermediates, as the relief of ring-strain provides a driving force for efficient ring-opening or ring-expansion reactions. Furthermore, the vinyl group can be derivatized into interesting functionalities. The ring-closure of vicinal amino alcohols constitutes a straightforward route to aziridines. Several methods exist for this transformation, although many cannot be applied to vinylaziridines due to their acid lability. This comparative study describes the most effective sequences for the formation of N-H vinylaziridines.
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| 8. |
- Olofsson, Berit, et al.
(författare)
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Vinylepoxides in Organic Synthesis
- 2006
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Ingår i: Aziridines and Epoxides in Organic Synthesis. - Weinheim, FRG : John Wiley & Sons. - 9783527312139 ; , s. 315-347
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Bokkapitel (refereegranskat)
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