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Enantioselective Synthesis of 6,6‐Disubstituted Pentafulvenes Containing a Chiral Pendant Hydroxy Group
Author(s) -
Nouch Ryan,
Cini Melchior,
Magre Marc,
Abid Mohammed,
Diéguez Montserrat,
Pàmies Oscar,
Woodward Simon,
Lewis William
Publication year - 2017
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.201704247
Subject(s) - fulvene , enantioselective synthesis , cyclopentadiene , carbanion , chemistry , bicyclic molecule , reactivity (psychology) , condensation , organic chemistry , stereochemistry , catalysis , physics , alternative medicine , pathology , thermodynamics , medicine
Simple enantioselective synthesis of 6,6‐disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline‐based organocatalysts. Condensation of cyclopentadiene with the acetyl function of a 1,2‐formylacetophenone, followed by cyclization of a resulting fulvene‐stabilized carbanion with the formyl group, generates bicyclic chiral alcohols with initial er values up to 94:6. Exceptional enantio‐enrichment of the resultant alcohols results upon crystallization—even near racemic samples spontaneously de‐racemize. This enables new families of substituted cyclopentadienes that are both enantiomerically and diastereomerically pure to be rapidly attained.