Compositions and methods for making donor-acceptor azetines
US11377420B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jun 24, 2020 |
| Grant date | Jul 5, 2022 |
| Priority date | — |
| Expiry date | Jun 24, 2040 |
Classification
- Technology area (CPC B)Performing Operations; Transporting
- CPC primaryB01J2531/16
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A highly effective synthetic route to produce donor-acceptor azetines through the highly enantioselective [3+1]-cycloaddition of silyl-protected enoldiazoacetates with aza-ylides using chiral copper(I) catalysis is provided. In one embodiment, the 2-azetidine cycloaddition products undergo generation of 3-azetidinones by reactions with nucleophiles that produce a broad spectrum of peptide products by the retro-Claisen reaction provided by facile strain with high efficacy and complete retention of enantiopurity. This ring opening reaction uncovers a new methodology for the attachment of chiral peptide units to a variety of amines and alcohols, and tolerates a broad scope of nucleophiles including naturally occurring amines, alcohols, amino acids, and other nitrogen based nucleophiles.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.