Cu-Catalyzed Asymmetric Synthesis of γ-Amino Alcohols Featuring Tertiary Carbon Stereocenters
Alkyne-functionalized oxetanes are presented as versatile substrates that in combination with amine reagents can be transformed into structurally diverse, chiral γ-amino alcohols featuring a tetrasubstituted tertiary stereocenter under Cu catalysis. Control experiments demonstrate the privileged nature of these oxetane precursors in terms of yield and asymmetric induction levels in the developed protocol, and postsynthetic modifications offer an easy way to access more advanced synthons.
Authors
- Alejandro Delgado (ORCID: https://orcid.org/0000-0002-9812-9405)
- Jordi Benet‐Buchholz (ORCID: https://orcid.org/0000-0003-3984-3550)
- Daniele Passarella (ORCID: https://orcid.org/0000-0001-6180-9581)
- Matteo Lanzi (ORCID: https://orcid.org/0000-0003-0254-7977)
- Paolo Orlando (ORCID: https://orcid.org/0000-0002-6576-9860)
- Arjan W. Kleij (ORCID: https://orcid.org/0000-0002-7402-4764)
Institutions
- Institució Catalana de Recerca i Estudis Avançats (ES)
- University of Milan (IT)
- Institut Català d'Investigació Química (ES)
- Universitat Rovira i Virgili (ES)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-30
- DOI
- https://doi.org/10.1021/acs.orglett.4c02682
- Citations
- 8
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.00
Funders
- Università degli Studi di Milano
- Ministerio de Ciencia, Innovación y Universidades
- Generalitat de Catalunya
- Institució Catalana de Recerca i Estudis Avançats
- Ministerio de Ciencia e Innovación
- Agència de Gestió d'Ajuts Universitaris i de Recerca