Premium
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.