Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles
The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselec...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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Royal Society of Chemistry
2015
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| _version_ | 1797054358932684800 |
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| author | Chintalapudi, V Galvin, E Greenaway, R Anderson, E |
| author_facet | Chintalapudi, V Galvin, E Greenaway, R Anderson, E |
| author_sort | Chintalapudi, V |
| collection | OXFORD |
| description | The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position. |
| first_indexed | 2024-03-06T18:56:10Z |
| format | Journal article |
| id | oxford-uuid:11e99d37-59b7-4386-b6e3-7269b6f97ebb |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:56:10Z |
| publishDate | 2015 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:11e99d37-59b7-4386-b6e3-7269b6f97ebb2022-03-26T10:04:53ZCombining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindolesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:11e99d37-59b7-4386-b6e3-7269b6f97ebbEnglishSymplectic Elements at OxfordRoyal Society of Chemistry2015Chintalapudi, VGalvin, EGreenaway, RAnderson, EThe synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position. |
| spellingShingle | Chintalapudi, V Galvin, E Greenaway, R Anderson, E Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles |
| title | Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles |
| title_full | Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles |
| title_fullStr | Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles |
| title_full_unstemmed | Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles |
| title_short | Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles |
| title_sort | combining cycloisomerization with trienamine catalysis a regiochemically flexible enantio and diastereoselective synthesis of hexahydroindoles |
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