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Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Oct 04; Vol. 60 (41), pp. 22224-22229. Date of Electronic Publication: 2021 Sep 07. - Publication Year :
- 2021
-
Abstract
- Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel Pd <superscript>II</superscript> -catalyst containing the imidazole-based P,N-ligand (S)-StackPhos is reported. The high-yielding reactions are operationally simple to perform with enantioselectivities up to 99 % ee. This strategy facilitates the replacement of a poor leaving group with what would ostensibly be a better leaving group in the product avoiding complications arising from racemization by equilibration.<br /> (© 2021 Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 60
- Issue :
- 41
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 34423520
- Full Text :
- https://doi.org/10.1002/anie.202108336