The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent.
The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in > 98% ee, on a multigram (> 25 g) scale. Conversion to a range of N-acyl derivatives, followed by...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2009
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| _version_ | 1797098802436374528 |
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| author | Chernega, A Davies, S Goodwin, C Hepworth, D Kurosawa, W Roberts, P Thomson, J |
| author_facet | Chernega, A Davies, S Goodwin, C Hepworth, D Kurosawa, W Roberts, P Thomson, J |
| author_sort | Chernega, A |
| collection | OXFORD |
| description | The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in > 98% ee, on a multigram (> 25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (> or = 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (> 98% de) after chromatography. Reductive cleavage with LiAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (> or = 94% ee). The auxiliary can be recovered in > 98% ee and recycled. |
| first_indexed | 2024-03-07T05:14:52Z |
| format | Journal article |
| id | oxford-uuid:dcd49f02-6731-4167-83e2-0a8f91cc30bb |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:14:52Z |
| publishDate | 2009 |
| record_format | dspace |
| spelling | oxford-uuid:dcd49f02-6731-4167-83e2-0a8f91cc30bb2022-03-27T09:20:29ZThe chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dcd49f02-6731-4167-83e2-0a8f91cc30bbEnglishSymplectic Elements at Oxford2009Chernega, ADavies, SGoodwin, CHepworth, DKurosawa, WRoberts, PThomson, JThe chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in > 98% ee, on a multigram (> 25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (> or = 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (> 98% de) after chromatography. Reductive cleavage with LiAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (> or = 94% ee). The auxiliary can be recovered in > 98% ee and recycled. |
| spellingShingle | Chernega, A Davies, S Goodwin, C Hepworth, D Kurosawa, W Roberts, P Thomson, J The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. |
| title | The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. |
| title_full | The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. |
| title_fullStr | The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. |
| title_full_unstemmed | The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. |
| title_short | The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. |
| title_sort | chiral auxiliary n 1 1 naphthyl ethyl o tert butylhydroxylamine a chiral weinreb amide equivalent |
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