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Rapid Synthesis of anti-1,3-Diamino-4-phenylbutan-2-ol Building Blocks via a Three-Component Oxyhomologation and a Two-Component Reducing System.
- Source :
-
ChemistryOpen [ChemistryOpen] 2024 Oct 30, pp. e202400279. Date of Electronic Publication: 2024 Oct 30. - Publication Year :
- 2024
- Publisher :
- Ahead of Print
-
Abstract
- N <superscript>1</superscript> -substituted derivatives of anti-(2R,3S)-1,3-diamino-4-phenylbutan-2-ol are important building blocks for the synthesis of therapeutically important molecules. We describe a simple protocol that allows transformation of N,N-dibenzyl-L-phenylalaninal into such compounds in only two steps. The first step is a fully stereoselective three-component MAC (Masked Acyl Cyanide) oxyhomologation reaction implicating different amines to give a panel of ten N,N-dibenzyl-O-tert-butyldimethylsilyl-protected anti-(2S,3S)-allophenylnorstatin amides. The second step is a carbonyl-activated hydride deprotection/reduction protocol using trimethylsilyl chloride and lithium aluminium hydride; the one-pot two-component system is more efficient than the alternative approach of isolating the deprotected amide intermediate before reduction.<br /> (© 2024 The Authors. ChemistryOpen published by Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 2191-1363
- Database :
- MEDLINE
- Journal :
- ChemistryOpen
- Publication Type :
- Academic Journal
- Accession number :
- 39473349
- Full Text :
- https://doi.org/10.1002/open.202400279