Abstract
An efficient route for the synthesis of enantiopure unnatural α-amino acids and 2-amino alcohols was developed. The synthesis is based on the Wittig-type olefination of 3-benzyloxy-2-(tertbutoxycarbonylamino)propanal with various ylides.
Highlights
The synthesis of unnatural amino acids has attracted special attention in recent years.[1,2]Unnatural amino acids play an important role in the design and synthesis of pharmacologically relevant molecules, peptidomimetics and enzyme inhibitors.[3,4,5] Aldehydes obtained from natural amino acids constitute a class of chiral synthons useful in the synthesis of optically active bioactive compounds and, in particular, in the synthesis of unnatural amino acids
N,N-bisBoc-glutamate and aspartate aldehydes 3 have been proposed as chiral intermediates for the synthesis of unnatural amino acids[8,9] and have found many applications.[10]
N-Protected αaminoaldehydes may be prepared either by reduction of a carboxy derivative of an amino acid or by oxidation of 2-aminoalcohols, and it is known that they have a high tendency for racemization.[19]
Summary
The synthesis of unnatural amino acids has attracted special attention in recent years.[1,2]Unnatural amino acids play an important role in the design and synthesis of pharmacologically relevant molecules, peptidomimetics and enzyme inhibitors.[3,4,5] Aldehydes obtained from natural amino acids constitute a class of chiral synthons useful in the synthesis of optically active bioactive compounds and, in particular, in the synthesis of unnatural amino acids. Synthesis and Wittig reactions of amino aldehyde 5. Our strategy to synthesize unnatural α-amino acids was based on a Wittig-type olefination reaction of aldehyde 5.
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