Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin
The asymmetric syntheses of (–)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (–)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-ope...
| Main Authors: | , , , , |
|---|---|
| Format: | Journal article |
| Published: |
American Chemical Society
2016
|
| _version_ | 1797085665490370560 |
|---|---|
| author | Davies, S Figuccia, A Fletcher, A Roberts, P Thomson, J |
| author_facet | Davies, S Figuccia, A Fletcher, A Roberts, P Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The asymmetric syntheses of (–)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (–)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-opening of the corresponding aziridinium intermediates with a tethered carbamate moiety) to give oxazolidin-2-ones was initially optimised on a model system. Subsequent application of this methodology to two enantiopure bishomoallylic amines (which were produced via aminohydroxylation of an α,β-unsaturated ester, partial reduction and reaction of the corresponding aldehyde with vinylmagnesium bromide) also proceeded with concomitant N-debenzylation to afford the corresponding diastereoisomerically pure (>99:1 dr) oxazolidin-2-ones. Subsequent deprotection of these enantiopure templates gave (–)-ADMJ and (+)-ADANJ as single diastereoisomers in 16 and 24% overall yield, respectively. |
| first_indexed | 2024-03-07T02:11:37Z |
| format | Journal article |
| id | oxford-uuid:a0d832f4-9694-44cb-aa60-77de6aae293d |
| institution | University of Oxford |
| last_indexed | 2024-03-07T02:11:37Z |
| publishDate | 2016 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:a0d832f4-9694-44cb-aa60-77de6aae293d2022-03-27T02:08:36ZAsymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-DeoxyallonojirimycinJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:a0d832f4-9694-44cb-aa60-77de6aae293dSymplectic Elements at OxfordAmerican Chemical Society2016Davies, SFiguccia, AFletcher, ARoberts, PThomson, JThe asymmetric syntheses of (–)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (–)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-opening of the corresponding aziridinium intermediates with a tethered carbamate moiety) to give oxazolidin-2-ones was initially optimised on a model system. Subsequent application of this methodology to two enantiopure bishomoallylic amines (which were produced via aminohydroxylation of an α,β-unsaturated ester, partial reduction and reaction of the corresponding aldehyde with vinylmagnesium bromide) also proceeded with concomitant N-debenzylation to afford the corresponding diastereoisomerically pure (>99:1 dr) oxazolidin-2-ones. Subsequent deprotection of these enantiopure templates gave (–)-ADMJ and (+)-ADANJ as single diastereoisomers in 16 and 24% overall yield, respectively. |
| spellingShingle | Davies, S Figuccia, A Fletcher, A Roberts, P Thomson, J Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin |
| title | Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin |
| title_full | Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin |
| title_fullStr | Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin |
| title_full_unstemmed | Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin |
| title_short | Asymmetric Syntheses of (–)-ADMJ and (+)-ADANJ: the 2-Deoxy-2-amino Analogues of (–)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin |
| title_sort | asymmetric syntheses of admj and adanj the 2 deoxy 2 amino analogues of 1 deoxymannojirimycin and 1 deoxyallonojirimycin |
| work_keys_str_mv | AT daviess asymmetricsynthesesofadmjandadanjthe2deoxy2aminoanaloguesof1deoxymannojirimycinand1deoxyallonojirimycin AT figucciaa asymmetricsynthesesofadmjandadanjthe2deoxy2aminoanaloguesof1deoxymannojirimycinand1deoxyallonojirimycin AT fletchera asymmetricsynthesesofadmjandadanjthe2deoxy2aminoanaloguesof1deoxymannojirimycinand1deoxyallonojirimycin AT robertsp asymmetricsynthesesofadmjandadanjthe2deoxy2aminoanaloguesof1deoxymannojirimycinand1deoxyallonojirimycin AT thomsonj asymmetricsynthesesofadmjandadanjthe2deoxy2aminoanaloguesof1deoxymannojirimycinand1deoxyallonojirimycin |