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An approach to the stereoselective synthesis of enantiopure dihydropyrroles and aziridines from a common sulfinyl-sulfinamide intermediate.
The diastereoselective addition of lithiated vinyl sulfoxides to enantiopure sulfinimines provides direct access to a wide assortment of allylic sulfinamides in good yields and excellent
[2,3]-Sigmatropic rearrangements of 3-sulfinyl dihydropyrans: application to the syntheses of the cores of ent-dysiherbaine and deoxymalayamicin A.
The [2,3]-sigmatropic rearrangement of a variety of configurationally stable diastereomeric allylic sulfinyl dihydropyrans, produced by base-promoted cyclization of sulfinyl dienols, has been
Sulfur-directed enantioselective synthesis of functionalized dihydropyrans.
TLDR
The highly selective base-promoted cyclization of enantiopure sulfinyl dienols affords allylic dihydropyranyl sulfones and sulfoximines in S(N)2' processes with organocuprates, and the reactivity of these products to dihydroxylation opens new possibilities to access enantio- and stereoselectivityated tetrahydropyrans that could be of interest for the synthesis of natural products.