Origin of the Diastereoselectivityof the HeterogeneousHydrogenation of a Substituted Indolizine
St Andrews Research Repository (St Andrews Research Repository)(2020)
摘要
In this work, the stereoselective
heterogeneous hydrogenation of
a tetrasubstituted indolizine was studied. Partial hydrogenation products
were obtained in three steps from a substituted pyridine-2-carboxaldehyde
prepared from commercial pyridoxine hydrochloride. The hydrogenation
of the indolizine ring was shown to be diastereoselective, forming trans-6b and cis-9. Theoretical calculations (ab initio and DFT) were
used to rationalize the unusual trans stereoselectivity
for 6b, and a keto–enol tautomerism under kinetic
control has been proposed as the source of diastereoselectivity.
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关键词
heterogeneoushydrogenation,diastereoselectivityof
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