Enantioselective Desymmetrization Triggered by Iminium‐Enamine Activation: Access to Complex Cycloheptaindoles
The expeditious construction of complex molecules having multiple stereocentres is highly desirable in organic chemistry. In the present communication, we report the development of an organocatalytic asymmetric desymmetrization of prochiral enal‐tethered cyclohexadienones via the C3‐selective Friede...
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| Veröffentlicht in: | Chemistry : a European journal 2023-03, Vol.29 (15) |
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| container_title | Chemistry : a European journal |
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| creator | Magham, Lakshmi Revati Thopate, Satish B Samad, Abdus Chegondi, Rambabu |
| description | The expeditious construction of complex molecules having multiple stereocentres is highly desirable in organic chemistry. In the present communication, we report the development of an organocatalytic asymmetric desymmetrization of prochiral enal‐tethered cyclohexadienones via the C3‐selective Friedel−Crafts alkylation of indoles triggered by LUMO‐lowering iminium activation/HOMO‐raising enamine activation. The reaction provides access to bicyclic enones, which further undergo acid‐mediated intramolecular annulation from C2‐position to afford highly strained cyclohepta[b]indoles with five contiguous stereocentres and three new C−C bonds in excellent enantioselectivity and diastereoselectivity. |
| doi_str_mv | 10.1002/chem.202203435 |
| format | Article |
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In the present communication, we report the development of an organocatalytic asymmetric desymmetrization of prochiral enal‐tethered cyclohexadienones via the C3‐selective Friedel−Crafts alkylation of indoles triggered by LUMO‐lowering iminium activation/HOMO‐raising enamine activation. The reaction provides access to bicyclic enones, which further undergo acid‐mediated intramolecular annulation from C2‐position to afford highly strained cyclohepta[b]indoles with five contiguous stereocentres and three new C−C bonds in excellent enantioselectivity and diastereoselectivity.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202203435</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkylation ; Chemical reactions ; Chemistry ; Enantiomers ; Indoles ; Molecular orbitals ; Organic chemistry ; Stereoselectivity</subject><ispartof>Chemistry : a European journal, 2023-03, Vol.29 (15)</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Magham, Lakshmi Revati</creatorcontrib><creatorcontrib>Thopate, Satish B</creatorcontrib><creatorcontrib>Samad, Abdus</creatorcontrib><creatorcontrib>Chegondi, Rambabu</creatorcontrib><title>Enantioselective Desymmetrization Triggered by Iminium‐Enamine Activation: Access to Complex Cycloheptaindoles</title><title>Chemistry : a European journal</title><description>The expeditious construction of complex molecules having multiple stereocentres is highly desirable in organic chemistry. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkylation Chemical reactions Chemistry Enantiomers Indoles Molecular orbitals Organic chemistry Stereoselectivity |
| title | Enantioselective Desymmetrization Triggered by Iminium‐Enamine Activation: Access to Complex Cycloheptaindoles |
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