L-vinyl glycine

The sulfur analog of the selenoxide pyrolysis is also known. In this sulfoxide pyrolysis the C-S bond is broken. The C-S bond is stronger than the C-Se bond and this explains why sulfoxides must typically be pyrolyzed at 200 °C to achieve elimination. Figure 4.13 shows the transformation of protected L-methionine into the corresponding sulfoxide, which then undergoes sulfoxide pyrolysis. This two-step sequence provides an elegant access to the nonnatural amino acid L-vinyl glycine. 

Fig. 4. 13. Sulfoxide pyrolysis for the formation of the C=C double bond of protected l-vinyl glycine, a non-proteino-genic amino acid.

N-[(Benzyloxy(carbonyl]-L-vinyl glycine Methyl Ester. 

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