A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction.
A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction...
Main Authors: | , , , |
---|---|
Format: | Journal article |
Language: | English |
Published: |
2011
|
_version_ | 1797051908782817280 |
---|---|
author | Sladojevich, F Trabocchi, A Guarna, A Dixon, D |
author_facet | Sladojevich, F Trabocchi, A Guarna, A Dixon, D |
author_sort | Sladojevich, F |
collection | OXFORD |
description | A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained. |
first_indexed | 2024-03-06T18:25:53Z |
format | Journal article |
id | oxford-uuid:07f1fb2c-c5ff-4308-84c5-31e4ab668865 |
institution | University of Oxford |
language | English |
last_indexed | 2024-03-06T18:25:53Z |
publishDate | 2011 |
record_format | dspace |
spelling | oxford-uuid:07f1fb2c-c5ff-4308-84c5-31e4ab6688652022-03-26T09:10:13ZA new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:07f1fb2c-c5ff-4308-84c5-31e4ab668865EnglishSymplectic Elements at Oxford2011Sladojevich, FTrabocchi, AGuarna, ADixon, DA new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained. |
spellingShingle | Sladojevich, F Trabocchi, A Guarna, A Dixon, D A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction. |
title | A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction. |
title_full | A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction. |
title_fullStr | A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction. |
title_full_unstemmed | A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction. |
title_short | A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction. |
title_sort | new family of cinchona derived amino phosphine precatalysts application to the highly enantio and diastereoselective silver catalyzed isocyanoacetate aldol reaction |
work_keys_str_mv | AT sladojevichf anewfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT trabocchia anewfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT guarnaa anewfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT dixond anewfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT sladojevichf newfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT trabocchia newfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT guarnaa newfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction AT dixond newfamilyofcinchonaderivedaminophosphineprecatalystsapplicationtothehighlyenantioanddiastereoselectivesilvercatalyzedisocyanoacetatealdolreaction |