Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions
One of the major challenges of modern asymmetric catalysis is the ability to selectively control the formation of all diastereoisomers of reaction products possessing multiple stereocenters. Pioneers of such diastereodivergent catalytic asymmetric processes have focused on reactions where the newly...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Journal article |
| Sprog: | English |
| Udgivet: |
Springer Nature
2014
|
| _version_ | 1826263538000199680 |
|---|---|
| author | Li, X Lu, M Dong, Y Wu, W Qian, Q Ye, J Dixon, D |
| author_facet | Li, X Lu, M Dong, Y Wu, W Qian, Q Ye, J Dixon, D |
| author_sort | Li, X |
| collection | OXFORD |
| description | One of the major challenges of modern asymmetric catalysis is the ability to selectively control the formation of all diastereoisomers of reaction products possessing multiple stereocenters. Pioneers of such diastereodivergent catalytic asymmetric processes have focused on reactions where the newly formed stereogenic centres are proximal to the active carbonyl group. To date, however, diastereodivergent reactions at remote positions remain an unmet challenge. Herein, we describe a catalyst-controlled diastereodivergence in the formation of remote stereocenters in the direct vinylogous Michael reactions of β, γ-unsaturated butenolides to α, β-unsaturated ketones. The reactions are enabled by two complementary, non-enantiomeric multifunctional catalysts, which mutually activate and organise both reactants, affording either the syn- or anti-adduct with high diastereo- and enantioselectivity. These two catalytic systems are also applicable in the Mukaiyama–Michael reactions and tandem Michael–Michael reactions. |
| first_indexed | 2024-03-06T19:53:22Z |
| format | Journal article |
| id | oxford-uuid:24b96aa6-8ee0-435d-a9ce-c3638b9a6466 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:53:22Z |
| publishDate | 2014 |
| publisher | Springer Nature |
| record_format | dspace |
| spelling | oxford-uuid:24b96aa6-8ee0-435d-a9ce-c3638b9a64662022-03-26T11:51:38ZDiastereodivergent organocatalytic asymmetric vinylogous Michael reactionsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:24b96aa6-8ee0-435d-a9ce-c3638b9a6466EnglishSymplectic Elements at OxfordSpringer Nature2014Li, XLu, MDong, YWu, WQian, QYe, JDixon, DOne of the major challenges of modern asymmetric catalysis is the ability to selectively control the formation of all diastereoisomers of reaction products possessing multiple stereocenters. Pioneers of such diastereodivergent catalytic asymmetric processes have focused on reactions where the newly formed stereogenic centres are proximal to the active carbonyl group. To date, however, diastereodivergent reactions at remote positions remain an unmet challenge. Herein, we describe a catalyst-controlled diastereodivergence in the formation of remote stereocenters in the direct vinylogous Michael reactions of β, γ-unsaturated butenolides to α, β-unsaturated ketones. The reactions are enabled by two complementary, non-enantiomeric multifunctional catalysts, which mutually activate and organise both reactants, affording either the syn- or anti-adduct with high diastereo- and enantioselectivity. These two catalytic systems are also applicable in the Mukaiyama–Michael reactions and tandem Michael–Michael reactions. |
| spellingShingle | Li, X Lu, M Dong, Y Wu, W Qian, Q Ye, J Dixon, D Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions |
| title | Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions |
| title_full | Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions |
| title_fullStr | Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions |
| title_full_unstemmed | Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions |
| title_short | Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions |
| title_sort | diastereodivergent organocatalytic asymmetric vinylogous michael reactions |
| work_keys_str_mv | AT lix diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions AT lum diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions AT dongy diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions AT wuw diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions AT qianq diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions AT yej diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions AT dixond diastereodivergentorganocatalyticasymmetricvinylogousmichaelreactions |