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Practical synthesis of α-amino acids using cis-aminoindanol derived hippuric acid amide as a glycine enolate equivalent

✍ Scribed by Jaemoon Lee; Woo-Baeg Choi; Joseph E Lynch; R.P Volante; P.J Reider


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
182 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis


The use of cis-aminoindanol as a chiral auxiliary for asymmetric synthesis of c~-amino acids is described. Alkylation of the chirally modified glycine enolate 2 with a number of alkyl halides in the presence of lithium chloride gave the corresponding alkylated product in 90 -99% diastereoselectivity.


📜 SIMILAR VOLUMES


Asymmetric alkylations of a sultam-deriv
✍ Wolfgang Oppolzer; Robert Moretti; Silvia Thomi 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 155 KB

Deprotonation/alkylation of sultam-derived N-[bis(methyl)thiomethylene]glycinate equivalent 2 gave crystalline products 5 which on mild hydrolysis furnished a-amino acids 2 (-100% e.e.) in high overall yield. Chiral glycine equivalents represent an attractive pivotal source for asymmetric syntheses