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Preparation of (±)-α-alkylated amino acid derivatives via imidazoles

✍ Scribed by Bruce H Lipshutz; Bret Huff; Wayne Vaccaro

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
256 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Photooxidation of N-methoxy-2.4-disubstituted imidasoles, readily available by way of a three component cyclization followed by 0-allcylation, leads to stable acyl imines whhich react with various organometallics to afford cr,a-disubstituted amino acid m-amides in good yields.

In an earlier communication2 from these laboratories a method was described for converting 1,2,4_trisubstituted imidazoles 1 to amino acid b-amides (i.e., 4). Treatment of variously derivatixed systems 1 with singlet oxygen, followed by base-induced isomerixation of the initial photoadducts 2 with KO-f-Baa, gives dehydroamino acid derivatives 2. These hydrogenate nicely under the influence of a chiral catalyst to amino acid m-amides fi of high ee's. Also noted with great interest was the finding that acyl imines 2 cleanly and regiospecifically

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