Synthesis of Sulfur-Containing Exo-Bicyclic Dienes and Their Diels–Alder Reactions To Access Thiacycle-Fused Polycyclic Systems | Zendy

Thomas Castanheiro | Zendy; Angèle Schoenfelder | Zendy; Morgan Donnard | Zendy; Isabelle Chataigner | Zendy; Mihaela Gulea | Zendy

Open Access

Synthesis of Sulfur-Containing Exo-Bicyclic Dienes and Their Diels–Alder Reactions To Access Thiacycle-Fused Polycyclic Systems

Author(s) -

Thomas Castanheiro,

Angèle Schoenfelder,

Morgan Donnard,

Isabelle Chataigner,

Mihaela Gulea

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b00213

Subject(s) - bicyclic molecule , chemistry , reactivity (psychology) , diene , sulfur , palladium , diels–alder reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology

The stereocontrolled synthesis of unprecedented sulfur-containing exo-bicyclic 1,3-dienes is reported through a palladium-catalyzed reductive cyclization of sulfur-linked 2-bromoenynes. The fused bicyclic structure provides a better stability to the thiacyclic diene compared to the simple 3,4-dimethylenetetrahydrothiophene. Their reactivity toward several dienophiles has been investigated, and various original thiacycle-fused polycyclic systems have been obtained with high or total diastereoselectivity. Moreover, they are the first exo-bicyclic dienes used in Diels-Alder reactions. The relative configurations of four cycloadducts have been unambiguously assigned by X-ray crystallographic analysis. Mechanistic details of the cycloadditions have been examined by computational means.

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