AI Article Synopsis
- The text outlines a process that transforms N-Boc-protected l-amino acid methyl esters into enantiopure N-Boc allylamines through a modified Julia olefination method.
- It highlights key steps such as the reaction of a lithiated phenylalkylsulfone with amino esters, producing chiral β-ketosulfones, followed by the reductive elimination of α-acetoxysulfones.
- The described method is executed under mild conditions, leads to good yields, and maintains stereochemical integrity, making it more efficient than the traditional Julia reaction of α-amino aldehydes.
Article Abstract
The four-step conversion of a series of N-Boc-protected l-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273449 | PMC |
| http://dx.doi.org/10.3390/molecules21060805 | DOI Listing |
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