Stereoselective Synthesis of a Series of New  N ‐Alkyl‐3‐hydroxypiperidine Derivatives Containing a Hemiketal | Zendy

Wang Haibo | Zendy; Luo Hairong | Zendy; Ma Xiaofeng | Zendy; Zou Wei | Zendy; Shao Huawu | Zendy

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Stereoselective Synthesis of a Series of New N ‐Alkyl‐3‐hydroxypiperidine Derivatives Containing a Hemiketal

Author(s) -

Wang Haibo,

Luo Hairong,

Ma Xiaofeng,

Zou Wei,

Shao Huawu

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201100533

Subject(s) - chemistry , intramolecular force , cycloaddition , stereoselectivity , alkyl , stereochemistry , methanol , intramolecular reaction , organic chemistry , catalysis

A series of new N ‐alkyl‐3‐hydroxypiperidine derivatives containing a five‐membered hemiketal were synthesized from 1‐ C ‐acetylmethyl sugars. Based on the stereochemistry of the products obtained, a plausible mechanism is illustrated. A new approach to the hemiketal, which has undergone hydrogenation in the presence of Pd/C and β‐elimination and intramolecular cycloaddition with 1 % NaOMe in methanol, is reported.

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