Mannich Reactions of Carbohydrate Derivatives with Ketones To Afford Polyoxy-Functionalized Piperidines | Zendy

Lingaiah Maram | Zendy; Fujie Tanaka | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Mannich Reactions of Carbohydrate Derivatives with Ketones To Afford Polyoxy-Functionalized Piperidines

Author(s) -

Lingaiah Maram,

Fujie Tanaka

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b00105

Subject(s) - chemistry , iminium , piperidine , nucleophile , ketone , mannich reaction , bicyclic molecule , organic chemistry , carbohydrate , combinatorial chemistry , ion , catalysis

Mannich reactions of carbohydrate derivatives with ketones that afford polyoxy-functionalized piperidines are reported. Ketone nucleophiles (enamines/enolates) were generated in the presence of the amines used for the formation of the iminium ions of sugar derivatives with or without an additive. Conditions to preferentially generate piperidine derivatives rather than tetrahydrofurans were identified. Products from the reactions of allyl ketones were readily transformed to bicyclic piperidines.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research