Asymmetric Synthesis of β-Amino-α-Hydroxy Acids through Lewis Acid-Mediated Addition of Ketene Acetal to Imines

Asymmetric synthesis of β-amino-α-hydroxy acids, key components of medicinally important molecules including Paclitaxel, KRI-1314, amastatin, and microginin, has been attained from the aldimine coupling of chiral imines N-alkylidene-(S)- or (R)-α-methylbenzylamine with (Z)-α-methoxyketene methyltrim...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 74; no. 9; pp. 1667 - 1672
Main Authors Ha, Hyun-Joon, Ahn, Young-Gil, Woo, Jun-Sik, Lee, Gwan Sun, Lee, Won Koo
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.09.2001
Chemical Soc Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PRACTICAL SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
CYCLOHEXYLNORSTATINE
ESTER UNITS
(2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
TAXOL SIDE-CHAIN
RENIN INHIBITOR
(3R)-3-AMINODECANOIC ACID
DERIVATIVES
STEREOSELECTIVE SYNTHESIS
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Summary:Asymmetric synthesis of β-amino-α-hydroxy acids, key components of medicinally important molecules including Paclitaxel, KRI-1314, amastatin, and microginin, has been attained from the aldimine coupling of chiral imines N-alkylidene-(S)- or (R)-α-methylbenzylamine with (Z)-α-methoxyketene methyltrimethylsilyl acetal, followed by demethylation, hydrogenolysis, and hydrolysis.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.74.1667