Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals
The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc)<sub>2</sub> and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5...
Saved in:
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/29/23/5812 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850107118039859200 |
|---|---|
| author | Rayala Naveen Kumar Seongmin Lee |
| author_facet | Rayala Naveen Kumar Seongmin Lee |
| author_sort | Rayala Naveen Kumar |
| collection | DOAJ |
| description | The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc)<sub>2</sub> and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal. Presumably, the formation of 5/5-spiroiminals occurs through aminyl radical-mediated cyclization followed by amine-to-imine oxidation. |
| format | Article |
| id | doaj-art-bea00211b2774b5b8f9cd4bf0e6dc00c |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-bea00211b2774b5b8f9cd4bf0e6dc00c2025-08-20T02:38:39ZengMDPI AGMolecules1420-30492024-12-012923581210.3390/molecules29235812Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-SpiroiminalsRayala Naveen Kumar0Seongmin Lee1The Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USAThe Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USAThe hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc)<sub>2</sub> and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal. Presumably, the formation of 5/5-spiroiminals occurs through aminyl radical-mediated cyclization followed by amine-to-imine oxidation.https://www.mdpi.com/1420-3049/29/23/5812hypervalent iodinespiroiminalC-H activationSteroids |
| spellingShingle | Rayala Naveen Kumar Seongmin Lee Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals Molecules hypervalent iodine spiroiminal C-H activation Steroids |
| title | Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals |
| title_full | Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals |
| title_fullStr | Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals |
| title_full_unstemmed | Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals |
| title_short | Hypervalent Iodine-Mediated Synthesis of Steroidal 5/5-Spiroiminals |
| title_sort | hypervalent iodine mediated synthesis of steroidal 5 5 spiroiminals |
| topic | hypervalent iodine spiroiminal C-H activation Steroids |
| url | https://www.mdpi.com/1420-3049/29/23/5812 |
| work_keys_str_mv | AT rayalanaveenkumar hypervalentiodinemediatedsynthesisofsteroidal55spiroiminals AT seongminlee hypervalentiodinemediatedsynthesisofsteroidal55spiroiminals |