Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent
✍ Scribed by Martin J. O'Donnell; Francisca Delgado; Mark D. Drew; Richard S. Pottorf; Changyou Zhou; William L. Scott
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 332 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
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
Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to a-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.
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