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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.