ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A New Synthetic Route to β,α-Unsaturated α-Amino AcidsA versatile new synthetic pathway for the preparation of βγ-unsaturated α-amino acids (1) is presented. Cu(I)-catalyzed addition of ethyl isocyanoacetate (2) to α-chloro carbonyl compounds (3) gives 5-chloroalkyl-2-oxazolin-4-carboxylates (4) in high yields. A reductive elimination on 4 by means of zinc yields the N-formyl derivatives of βγ-unsaturated α-amino carboxylates (5), which on acid hydrolysis lead to the free amino acids 1. The five different βγ-dehydro-α-amono acids 1b-1f have been prepared by this method.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640734
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