Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated
✍ Scribed by Shū Kobayashi; Mineko Horibe; Yumi Saito
- Book ID
- 104203344
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 967 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Diastereo-and enantioselective synthesis of both diastereomers, including the aalkoxy-f&hydroxy-B-methyl(pheny1)
units, was performed by using chiral tin(ll) Lewis acidmediated asymmetric aldol reactions of a-alkoxy silyl en01 ethers with a-ketoesters.
(S-l-Propyl-2- [(1,2,3,4-tetrahydroisoquinolinyl))methyllpyrrolidine ( ), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-I-ethylthio-I-(trimethylsiloxy~ethene (9) with aldehydes for the synthesis of optically active syn-a,&dihydroxy thioester derivatives. (-)-2-C-Methyl-Derythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.