Abstract
The reaction of methyl 2-diazophenylacetate 1 and dimethyl α-diazobenzylphosphonate 2 with various N-H components in the presence of chiral dirhodium(II) catalysts results in N-H insertion in good yield but with little or no stereoselectivity.
Highlights
The synthesis of α-amino acids and peptides remains a topic of considerable importance and current interest
In previous papers,[2,3] we have reported that diazoesters react with a range of R3NH2 compounds in the presence of dirhodium(II) catalysts to give α-amino acid derivatives, the products of N-H insertion of the intermediate rhodium carbene, in high yield (Scheme 1)
In an extension to this work,[4] we showed that N-protected amino acid amides underwent N-H insertion reaction, in a new approach to dipeptides (Scheme 2)
Summary
The synthesis of α-amino acids and peptides remains a topic of considerable importance and current interest. This crude product was subjected to flash silica gel chromatography using light petroleum and ethyl acetate (9:1) as eluent to yield N-(4-dodecylphenylsulfonyl)-(S)-leucine methyl ester as a colourless oil (1.01 g, 2.23 mmol, 77%), [α]D20 +6.0 (c=1.0, CHCl3);
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