Increasing the Dimensionality of Modular Domino Reactions Triggered by Oxidative Cleavage: A Two‐Step Protocol Towards a Variety of Stereodefined Complex Oxygen Heterocycles | Zendy

Castillo Rafael R. | Zendy; Abet Valentina | Zendy; Aquino Maurizio | Zendy; Gandara Zoila | Zendy; Retailleau Pascal | Zendy; Arseniyadis Siméon | Zendy

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Increasing the Dimensionality of Modular Domino Reactions Triggered by Oxidative Cleavage: A Two‐Step Protocol Towards a Variety of Stereodefined Complex Oxygen Heterocycles

Author(s) -

Castillo Rafael R.,

Abet Valentina,

Aquino Maurizio,

Gandara Zoila,

Retailleau Pascal,

Arseniyadis Siméon

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201201483

Subject(s) - intramolecular force , domino , chemistry , oxidative phosphorylation , cleavage (geology) , oxidative cleavage , stereochemistry , combinatorial chemistry , cascade reaction , modular design , nucleophilic substitution , computer science , organic chemistry , materials science , catalysis , biochemistry , programming language , fracture (geology) , composite material

Arylcarbinol‐ and benzyl‐tethered octalin‐diols ( 1 / 1′ ), which differ only by the C11 substitution at the angular position, were transformed selectively into original scaffolds of high complexity through a two‐step protocol. Overall, the (11 S *) configuration ensures an intramolecular Friedel–Crafts‐type C13–C4 bonding through a domino process triggered by oxidative cleavage, whereas the (11 R *) configuration allows for a Marson‐type Friedel–Crafts C13–C2 bonding through an intramolecular nucleophilic acetal opening.

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