Monoalkylation of the a-amino group of or-amino acid derivatives can be facilitated using 2and 4-nitrophenylsulfonamide intermediates. The nitrophenylsulfonamides of a-amino esters can be alkylated using an equimolar amount of carbonate base and a variety of alkyl bromides. Ready removal of the nitr
An Aza-Enolate Alkylation Strategy for the Synthesis of α-Alkyl-δ-amino Esters and α-Alkyl Valerolactams.
✍ Scribed by Piers J. M. Taylor; Steven D. Bull; Philip C. Andrews
- Book ID
- 101993467
- Publisher
- John Wiley and Sons
- Year
- 2006
- Weight
- 24 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0931-7597
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📜 SIMILAR VOLUMES
O-Silylated ketone enolates can be alkylated regiospecifically with t-alkyl halides in the presence of an equivalent of titanium tetrachloride; 2 for the alkylation of lithium enolates, in general, dialkylation,3 loss of regiospecificity,3 and self-condensation4 are common problems. Alternative me
Deprotonation of alanine ester imines with KO'Bu in DMSO or DMF and alkylation of the formed enolates with several 2-fluoroalkyl halogenides 2 and subsequent hydrolysis of the imino and the ester groups are presented as an efficient three-step sequence for the synthesis of racemic title compounds 5.
## Abstract Deprotonation of __N__‐protected esters of the amino acids alanine 1, ethylglycin 6, valine 7, and phenylalanine 8 with LDA and subsequent addition of various metal salts result in the formation of a probably chelated metal enolate. Aldol reactions of these enolates with aldehydes affor