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Sulfinyl‐Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes
Author(s) -
Colomer Ignacio,
Ureña Mercedes,
Viso Alma,
Fernández de la Pradilla Roberto
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905742
Subject(s) - stereoselectivity , dihydroxylation , surface modification , conjugated system , chemistry , conjugate , protonation , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , mathematics , ion , mathematical analysis , polymer
The chemo‐ and stereocontrolled functionalization of conjugated sulfinyl dienes in a cascade process that involves a conjugate addition, diastereoselective protonation and a [2,3]‐sigmatropic rearrangement is reported. Enantioenriched 1,4‐diol and 1,4‐aminoalcohol derivatives are obtained in a very straightforward manner. Further functionalization of these structures, including highly stereoselective epoxidation, dihydroxylation and the stereodivergent synthesis of several polyols in a controlled fashion is described.