Photochemical Deracemization of Allenes and Subsequent Chirality Transfer

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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).

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Photochemical Deracemization of Allenes and Subsequent Chirality Transfer ; volume:59 ; number:31 ; year:2020 ; pages:12785-12788 ; extent:4
Angewandte Chemie / International edition. International edition ; 59, Heft 31 (2020), 12785-12788 (gesamt 4)

Creator: Plaza, Manuel
Jandl, Christian
Bach, Thorsten

DOI: 10.1002/anie.202004797

URN: urn:nbn:de:101:1-2022061409173731528946

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Associated

Plaza, Manuel
Jandl, Christian
Bach, Thorsten

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