(1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene
The crystal structure of the title compound, C34H54N2O4, has been solved in order to prove the relative and absolute chirality of the newly-formed stereocentres which were established using an asymmetric Diels–Alder reaction at an earlier stage in the synthesis. This unprecedented stab...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2010-07-01
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| Series: | Acta Crystallographica Section E |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536810023998 |
| _version_ | 1818791608436391936 |
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| author | Stéphanie M. Guéret Peter D. W. Boyd Margaret A. Brimble |
| author_facet | Stéphanie M. Guéret Peter D. W. Boyd Margaret A. Brimble |
| author_sort | Stéphanie M. Guéret |
| collection | DOAJ |
| description | The crystal structure of the title compound, C34H54N2O4, has been solved in order to prove the relative and absolute chirality of the newly-formed stereocentres which were established using an asymmetric Diels–Alder reaction at an earlier stage in the synthesis. This unprecedented stable dialdimine contains a 14-membered ring and was obtained as the minor diastereoisomer in the Diels–Alder reaction. The absolute stereochemistry of the stereocentres of the acetal functionality was known to be R based on the use of a chiral (R)-trisubstituted dienophile derived from enantiopure (S)-glyceraldehyde. The assignment of the configuration in the dienophile and the title di-aldimine differs from (S)-glyceraldehyde due to a change in the priority order of the substituents. The crystal structure establishes the presence of six stereocentres all attributed to be R. The 14-membered ring contains two aldimine bonds [C—N = 1.258 (2) and 1.259 (2) Å]. It adopts a similar conformation to that proposed for trans–trans-cyclotetradeca-1,8-dienes. |
| first_indexed | 2024-12-18T15:14:03Z |
| format | Article |
| id | doaj.art-556bf2948fdb48418491c0c0d5b0cb11 |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-12-18T15:14:03Z |
| publishDate | 2010-07-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-556bf2948fdb48418491c0c0d5b0cb112022-12-21T21:03:34ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682010-07-01667o1778o177910.1107/S1600536810023998(1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-dieneStéphanie M. GuéretPeter D. W. BoydMargaret A. BrimbleThe crystal structure of the title compound, C34H54N2O4, has been solved in order to prove the relative and absolute chirality of the newly-formed stereocentres which were established using an asymmetric Diels–Alder reaction at an earlier stage in the synthesis. This unprecedented stable dialdimine contains a 14-membered ring and was obtained as the minor diastereoisomer in the Diels–Alder reaction. The absolute stereochemistry of the stereocentres of the acetal functionality was known to be R based on the use of a chiral (R)-trisubstituted dienophile derived from enantiopure (S)-glyceraldehyde. The assignment of the configuration in the dienophile and the title di-aldimine differs from (S)-glyceraldehyde due to a change in the priority order of the substituents. The crystal structure establishes the presence of six stereocentres all attributed to be R. The 14-membered ring contains two aldimine bonds [C—N = 1.258 (2) and 1.259 (2) Å]. It adopts a similar conformation to that proposed for trans–trans-cyclotetradeca-1,8-dienes.http://scripts.iucr.org/cgi-bin/paper?S1600536810023998 |
| spellingShingle | Stéphanie M. Guéret Peter D. W. Boyd Margaret A. Brimble (1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene Acta Crystallographica Section E |
| title | (1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene |
| title_full | (1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene |
| title_fullStr | (1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene |
| title_full_unstemmed | (1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene |
| title_short | (1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene |
| title_sort | 1r 6r 13r 18r z z 1 18 bis 4r 2 2 dimethyl 1 3 dioxolan 4 yl 3 16 dimethylene 8 20 diazadispiro 5 6 5 6 tetracosa 7 19 diene |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536810023998 |
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