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Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to ?-Hydroxylation of Tetralone-Derived ?-Keto Esters.

ABSTRACT: Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for ?-hydroxylation of tetralone-derived ?-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety.

SUBMITTER: Odagi M

PROVIDER: S-EPMC6331824 | biostudies-other | 2015 Jul

REPOSITORIES: biostudies-other

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Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters.

Odagi Minami M Takayama Kan K Sato Makoto M Yamanaka Masahiro M Nagasawa Kazuo K

Molecules (Basel, Switzerland) 20150710 7

Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety. ...[more]

PMID: 26184142

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