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A stereoselective procedure for the preparation of non-naturally occurring deoxy iminosugars belonging to L-series has been developed. The synthesis involves the construction of the key intermediate bicycle pyperidine 8, available in few steps by the coupling of the heterocyclic synthon 3 and the readily available Garner aldehyde 4.

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A new synthetic catalyst, capable of acting like an enzyme in the accomplishment of direct aldol reactions, is presented. Excellent results, in terms of chemical yields and diastereo-/ enantiomeric ratios, are reported for the catalyzed additions of cyclohexanone to variously substituted benzaldehydes.

No abstract