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
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