Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines.
A catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom by a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona-derived aminophosphine precatalyst and s...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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Wiley
2014
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| _version_ | 1797105654459006976 |
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| author | Ortín, I Dixon, D |
| author_facet | Ortín, I Dixon, D |
| author_sort | Ortín, I |
| collection | OXFORD |
| description | A catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom by a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona-derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99% ee) were obtained for a range of substrates. |
| first_indexed | 2024-03-07T06:50:24Z |
| format | Journal article |
| id | oxford-uuid:fc600183-3cc9-4642-9a4a-32ad4818e6e9 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:50:24Z |
| publishDate | 2014 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:fc600183-3cc9-4642-9a4a-32ad4818e6e92022-03-27T13:20:08ZDirect catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:fc600183-3cc9-4642-9a4a-32ad4818e6e9EnglishSymplectic Elements at OxfordWiley2014Ortín, IDixon, DA catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom by a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona-derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99% ee) were obtained for a range of substrates. |
| spellingShingle | Ortín, I Dixon, D Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines. |
| title | Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines. |
| title_full | Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines. |
| title_fullStr | Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines. |
| title_full_unstemmed | Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines. |
| title_short | Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines. |
| title_sort | direct catalytic enantio and diastereoselective mannich reaction of isocyanoacetates and ketimines |
| work_keys_str_mv | AT ortini directcatalyticenantioanddiastereoselectivemannichreactionofisocyanoacetatesandketimines AT dixond directcatalyticenantioanddiastereoselectivemannichreactionofisocyanoacetatesandketimines |