Photochemical Deracemization of Allenes and Subsequent Chirality Transfer
Abstract: Trisubstituted allenes with a 3‐(1′‐alkenylidene)‐pyrrolidin‐2‐one motif were successfully deracemized (13 examples, 86–98 % ee) employing visible light (λ=420 nm) and a chiral triplet sensitizer as the catalyst (2.5 mol %). The photocatalyst likely operates by selective recognition of one allene enantiomer via hydrogen bonds and by a triplet‐sensitized racemization process. Even a tetrasubstituted allene (45 % ee) and a seven‐membered 3‐(1′‐alkenylidene)‐azepan‐2‐one (62 % ee) could be enantiomerically enriched under the chosen conditions. It was shown that the axial chirality of the allenes can be converted into point chirality by a Diels–Alder (94–97 % ee) or a bromination reaction (91 % ee). Ring opening of the five‐membered pyrrolidin‐2‐one was achieved without significantly compromising the integrity of the chirality axis (92 % ee).
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Photochemical Deracemization of Allenes and Subsequent Chirality Transfer ; volume:132 ; number:31 ; year:2020 ; pages:12885-12888 ; extent:4
Angewandte Chemie ; 132, Heft 31 (2020), 12885-12888 (gesamt 4)
- Urheber
- DOI
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10.1002/ange.202004797
- URN
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urn:nbn:de:101:1-2022053107352981841064
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:35 MESZ
Datenpartner
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Beteiligte
- Plaza, Manuel
- Jandl, Christian
- Bach, Thorsten
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