Ryan Nouch
Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group
Nouch, Ryan; Cini, Melchior; Magre, Marc; Abid, Mohammed; Di�guez, Monserrat; P�mies, Oscar; Woodward, Simon; Lewis, William
Authors
Melchior Cini
Marc Magre
Mohammed Abid
Monserrat Di�guez
Oscar P�mies
SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry
William Lewis
Abstract
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.
Journal Article Type | Article |
---|---|
Acceptance Date | Oct 26, 2017 |
Online Publication Date | Oct 30, 2017 |
Deposit Date | Nov 1, 2017 |
Publicly Available Date | Oct 31, 2018 |
Journal | Chemistry - a European Journal |
Print ISSN | 0947-6539 |
Electronic ISSN | 1521-3765 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
DOI | https://doi.org/10.1002/chem.201704247 |
Public URL | https://nottingham-repository.worktribe.com/output/891038 |
Publisher URL | http://onlinelibrary.wiley.com/doi/10.1002/chem.201704247/abstract |
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