| 1. |
|
|
| 2. |
|
|
| 3. |
|
|
| 4. |
- Deiana, Luca, et al.
(författare)
-
Catalytic Asymmetric Aziridination of alpha,beta-Unsaturated Aldehydes
- 2011
-
Ingår i: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 17:28, s. 7904-7917
-
Tidskriftsartikel (refereegranskat)abstract
- The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziridines with up to >19:1 d.r. and 99 % ee. The aminocatalytic aziridination of α-monosubstituted enals gives access to terminal α-substituted-α-formyl aziridines in high yields and up to 99 % ee. In the case of the organocatalytic aziridination of disubstituted α,β-unsaturated aldehydes, the transformations were highly diastereo- and enantioselective and give nearly enantiomerically pure β-formyl-functionalized aziridine products (99 % ee). A highly enantioselective one-pot cascade sequence based on the combination of asymmetric amine and N-heterocyclic carbene catalysis (AHCC) is also disclosed. This one-pot three-component co-catalytic transformation between α,β-unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N-tert-butoxycarbonyl and N-carbobenzyloxy-protected β-amino acid esters with ee values ranging from 92-99 %. The mechanisms and stereochemistry of all these catalytic transformations are also discussed.
|
|
| 5. |
- Deiana, Luca, 1982-, et al.
(författare)
-
Catalytic asymmetric aziridination of α,β-unsaturated aldehydes
- 2011
-
Ingår i: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 17:28, s. 7904-7917
-
Tidskriftsartikel (refereegranskat)abstract
- The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziridines with up to >19:1 d.r. and 99% ee. The aminocatalytic aziridination of α-monosubstituted enals gives access to terminal α-substituted-α-formyl aziridines in high yields and upto 99% ee. In the case of the organocatalytic aziridination of disubstituted α,β-unsaturated aldehydes, the transformations were highly diastereo- and enantioselective and give nearly enantiomerically pure β-formyl-functionalized aziridine products (99% ee). A highly enantioselective one-pot cascade sequence based on the combination of asymmetric amine and N-heterocycliccarbene catalysis (AHCC) is also disclosed. This one-pot three-component co-catalytic transformation between α,β-unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N-tert-butoxycarbonyl and N-carbobenzyloxy-protected β-amino acid esters with ee values ranging from 92–99%. The mechanisms and stereochemistry of all these catalytic transformations are also discussed.
|
|
| 6. |
- Deiana, Luca, et al.
(författare)
-
Catalytic asymmetric aziridination of α, β- unsaturated aldehydes
- 2011
-
Ingår i: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011. - : American Chemical Society.
-
Konferensbidrag (övrigt vetenskapligt/konstnärligt)abstract
- The development, scope and application of the highly enantioselective organocatalytic aziridination of a, b- unsaturated aldehydes is presented. The aminocatalytic aziridination of a, b- unsaturated aldehydes enables the asymmetric formation of b-formylaziridines with up to >19:1 dr and 99% ee. The aminocatalytic aziridination of a-monosobstituted enals gives access to terminal a-substituted-a-formyl aziridines in high yields and up to 99% ee. In the case of the organocatalytic aziridination of disubstituted a, b-unsaturated aldehydes, the transformations gives nearly enantiomeric pure b-formyl-functionalized aziridine products. A higly enantioselective one-pot cascade sequence based on combination of asymmetric amine and N-heterocyclic carbene catalysis is also disclosed. This transformation gives the corresponding N-Boc and N-Cbz protected b-amino acid esters with ee´s ranging from 92-99%.
|
|
| 7. |
- Deiana, Luca, 1982-, et al.
(författare)
-
Direct Catalytic Asymmetric Synthesis of Pyrazolidine Derivatives
- 2012
-
Ingår i: ChemistryOpen. - : Wiley. - 2191-1363. ; 1:3, s. 134-139
-
Tidskriftsartikel (refereegranskat)abstract
- A highly enantioselective, metal-free cascade reaction between di-1,2-N-protected hydrazine and α,β-unsaturated aldehydes is disclosed. The catalytic, asymmetric cascade transformation is a direct entry to 3-hydroxypyrazolidine and 3-allylpyrazolidine derivatives in one step and two steps, respectively, with >19:1 d.r. and 98–99 % ee using simple chiral pyrrolidines as catalysts.
|
|
| 8. |
|
|
| 9. |
|
|
| 10. |
|
|
