A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones.
A new family of bifunctional H-bond donor phase-transfer catalysts derived from cinchona alkaloids has been developed and evaluated in the enantio- and diastereoselective nitro-Mannich reaction of in situ generated N-Boc-protected imines of aliphatic, aromatic, and heteroaromatic aldehydes. Under op...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2012
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| _version_ | 1826296579650224128 |
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| author | Johnson, K Rattley, MS Sladojevich, F Barber, D Nuñez, MG Goldys, A Dixon, D |
| author_facet | Johnson, K Rattley, MS Sladojevich, F Barber, D Nuñez, MG Goldys, A Dixon, D |
| author_sort | Johnson, K |
| collection | OXFORD |
| description | A new family of bifunctional H-bond donor phase-transfer catalysts derived from cinchona alkaloids has been developed and evaluated in the enantio- and diastereoselective nitro-Mannich reaction of in situ generated N-Boc-protected imines of aliphatic, aromatic, and heteroaromatic aldehydes. Under optimal conditions, good reactivity and high diastereoselectivities (up to 24:1 dr) and enantioselectivities (up to 95% ee) were obtained using a 9-amino-9-deoxyepiquinidine-derived phase-transfer catalyst possessing a 3,5-bis(trifluoromethyl)phenylurea H-bond donor group at the 9-position. |
| first_indexed | 2024-03-07T04:18:31Z |
| format | Journal article |
| id | oxford-uuid:ca3b0e6e-471c-4a05-bfc7-3151975e3c69 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:18:31Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:ca3b0e6e-471c-4a05-bfc7-3151975e3c692022-03-27T07:05:52ZA new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ca3b0e6e-471c-4a05-bfc7-3151975e3c69EnglishSymplectic Elements at Oxford2012Johnson, KRattley, MSSladojevich, FBarber, DNuñez, MGGoldys, ADixon, DA new family of bifunctional H-bond donor phase-transfer catalysts derived from cinchona alkaloids has been developed and evaluated in the enantio- and diastereoselective nitro-Mannich reaction of in situ generated N-Boc-protected imines of aliphatic, aromatic, and heteroaromatic aldehydes. Under optimal conditions, good reactivity and high diastereoselectivities (up to 24:1 dr) and enantioselectivities (up to 95% ee) were obtained using a 9-amino-9-deoxyepiquinidine-derived phase-transfer catalyst possessing a 3,5-bis(trifluoromethyl)phenylurea H-bond donor group at the 9-position. |
| spellingShingle | Johnson, K Rattley, MS Sladojevich, F Barber, D Nuñez, MG Goldys, A Dixon, D A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. |
| title | A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. |
| title_full | A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. |
| title_fullStr | A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. |
| title_full_unstemmed | A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. |
| title_short | A new family of cinchona-derived bifunctional asymmetric phase-transfer catalysts: application to the enantio- and diastereoselective nitro-Mannich reaction of amidosulfones. |
| title_sort | new family of cinchona derived bifunctional asymmetric phase transfer catalysts application to the enantio and diastereoselective nitro mannich reaction of amidosulfones |
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