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The Alkyl -- proposed synthesis Haverford College #403
Proposed synthetic routes have been developed in collaboration with students as part of an organic chemistry class I teach at Haverford College. The molecules are seen as being desirable targets as per #390. This Issue has been created for community feedback on the routes, which can then be attempted in the lab by us or others.
Sonogashira reaction would give a triple bond. If we choose to generate an alkene we can pick a stereoselective reaction. @drc007 suggested Lindlar reduction, which leads to the syn-addition of H to give the cis isomer. Dissolving metal reductions would favour trans. Although of course sometimes we get a mixture of isomers, chromatographic separation is possible, silver nitrate columns can also be employed in trickier cases. It would be nice to test both geometries of course.