2-acetylthiazole as a three-carbon homologating reagent of aldehydes. Application toward the synthesis of amino hexoses from L-serinal
✍ Scribed by Alessandro Dondoni; Giancarlo Fantin; Marco Fogagnolo
- Book ID
- 104244937
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 277 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
P-Acetylthiazole (1) serves as a source of the a-hydroxypropanal b-anion synthon for the conversion of aldehydes into syn and antia.r-dihydroxy homologues with three-more carbon atoms via a sequence consisting of : i) aldol condensation of the lithium enolate derived from 1; ii) reduction of the hydroxy ketone; iii) thiazole to formyl unmasking. The methodology is employed for the conversion of L-serinal into amino sugars. In recent reports from this laboratory we have demonstrated the synthetic utility of P-substituted thiazoles as effective equivalents to aldehyde synthons in stereoselective methodologies directed toward the synthesis of long-chain 1,2-polyhydroxylated compounds (Thiazole Route).l Several advantages arise from the use of thiazoles as auxiliaries