Sulfinyl‐Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes | Zendy

Colomer Ignacio | Zendy; Ureña Mercedes | Zendy; Viso Alma | Zendy; Fernández de la Pradilla Roberto | Zendy

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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.

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