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[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.
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.
Stereoselective Functionalization of Dihydropyran‐3‐ols: Application to the Synthesis of Enantiopure Ethyl Deoxymonate B
Funded by: Direccion General de Investigacion, Ministerio de Educacion y Ciencia (DGI-MEC); Grant Number: CTQ2006-04522/BQU Comunidad de Madrid; Grant Number: S-SAL-0249-2006 Ministerio de
Highly Diastereoselective [3+2] Cycloadditions Between Non-Racemic p-Tolylsulfinimines and Iminoesters: An Efficient Entry to Enantiopure Imidazolidines and Vicinal Diaminoalcohols
P-tolylsulfinimines undergo highly stereoselective [3 + 2] cycloadditions with azomethine ylides generated from α -iminoesters and LDA to produce N-sulfinylimidazolidines, which have been transformed into examples of a novel class of nonsymmetrical vicinal diamines using reductive and/or hydrolytic protocols.