OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))]
The lithium enolate derived from the chiral iron acetyl complex (RS)-[(C5H5)Fe(CO)(PPh3)COCH3] (RS)-1 opens, in the presence of boron trifluoride etherate, the carbohydrate 5,6-epoxides, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 3, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-t...
| Main Authors: | , , |
|---|---|
| פורמט: | Journal article |
| שפה: | English |
| יצא לאור: |
1994
|
| _version_ | 1826300685029736448 |
|---|---|
| author | Davies, S Kellie, H Polywka, R |
| author_facet | Davies, S Kellie, H Polywka, R |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The lithium enolate derived from the chiral iron acetyl complex (RS)-[(C5H5)Fe(CO)(PPh3)COCH3] (RS)-1 opens, in the presence of boron trifluoride etherate, the carbohydrate 5,6-epoxides, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 3, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-talonofuranose 4, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 5, and 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofluranose 6 to generate after decomplexation the doubly homologated γ-lactones 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-allo-octafuranurono-5,8-lactone 15, 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-β-L-talono-octafuranurono-5,8-lactone 16, 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octafuranurono-5,8-lactone 17, and 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-β-L-ido-octafuranurono-5,8-lactone 18 respectively. The lithium enolate derived from the homochiral iron propionyl complexes (R)-[(C5H5)Fe(CO)(PPh3)COCH2CH3] (R)-2 and (S)-[(C5H5)Fe(CO)(PPh3)COCH3] (S)-2 convert after decomplexation 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 5 to 7(R)-methyl-3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octafuranurono-5,8-lactone 20 and 7(S)-methyl-3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octafuranurono-5,8-lactone 22 respectively. © 1994. |
| first_indexed | 2024-03-07T05:20:55Z |
| format | Journal article |
| id | oxford-uuid:dedd91e8-a9c3-42ef-a836-745f93d2758d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:20:55Z |
| publishDate | 1994 |
| record_format | dspace |
| spelling | oxford-uuid:dedd91e8-a9c3-42ef-a836-745f93d2758d2022-03-27T09:35:16ZOPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))]Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dedd91e8-a9c3-42ef-a836-745f93d2758dEnglishSymplectic Elements at Oxford1994Davies, SKellie, HPolywka, RThe lithium enolate derived from the chiral iron acetyl complex (RS)-[(C5H5)Fe(CO)(PPh3)COCH3] (RS)-1 opens, in the presence of boron trifluoride etherate, the carbohydrate 5,6-epoxides, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 3, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-talonofuranose 4, 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 5, and 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofluranose 6 to generate after decomplexation the doubly homologated γ-lactones 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-allo-octafuranurono-5,8-lactone 15, 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-β-L-talono-octafuranurono-5,8-lactone 16, 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octafuranurono-5,8-lactone 17, and 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-β-L-ido-octafuranurono-5,8-lactone 18 respectively. The lithium enolate derived from the homochiral iron propionyl complexes (R)-[(C5H5)Fe(CO)(PPh3)COCH2CH3] (R)-2 and (S)-[(C5H5)Fe(CO)(PPh3)COCH3] (S)-2 convert after decomplexation 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 5 to 7(R)-methyl-3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octafuranurono-5,8-lactone 20 and 7(S)-methyl-3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octafuranurono-5,8-lactone 22 respectively. © 1994. |
| spellingShingle | Davies, S Kellie, H Polywka, R OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))] |
| title | OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))] |
| title_full | OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))] |
| title_fullStr | OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))] |
| title_full_unstemmed | OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))] |
| title_short | OPENING OF CARBOHYDRATE 5,6-EPOXIDES WITH CHIRAL ACETATE AND PROPIONATE ENOLATE EQUIVALENTS ATTACHED TO THE IRON CHIRAL AUXILIARY [C5H5)FE(CO)(PPH(3))] |
| title_sort | opening of carbohydrate 5 6 epoxides with chiral acetate and propionate enolate equivalents attached to the iron chiral auxiliary c5h5 fe co pph 3 |
| work_keys_str_mv | AT daviess openingofcarbohydrate56epoxideswithchiralacetateandpropionateenolateequivalentsattachedtotheironchiralauxiliaryc5h5fecopph3 AT kellieh openingofcarbohydrate56epoxideswithchiralacetateandpropionateenolateequivalentsattachedtotheironchiralauxiliaryc5h5fecopph3 AT polywkar openingofcarbohydrate56epoxideswithchiralacetateandpropionateenolateequivalentsattachedtotheironchiralauxiliaryc5h5fecopph3 |