Carbohydrates as Chiral Templates: Stereoselective Tandem Mannich‐Michael Reactions for the Synthesis of Piperidine Alkaloids | Zendy

Kunz Horst | Zendy; Pfrengle Waldemar | Zendy

Premium

Carbohydrates as Chiral Templates: Stereoselective Tandem Mannich‐Michael Reactions for the Synthesis of Piperidine Alkaloids

Author(s) -

Kunz Horst,

Pfrengle Waldemar

Publication year - 1989

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198910671

Subject(s) - piperidine , diastereomer , stereoselectivity , mannich reaction , chemistry , anabasine , stereochemistry , template , michael reaction , tandem , catalysis , organic chemistry , alkaloid , materials science , composite material , nanotechnology

Pure diastereomers in high yields can be obtained by the reaction sequence shown below followed by crystallization or chromatography. The stereochemical course of the reaction is shown for R = n ‐propyl, p ‐chlorophenyl, and 2‐furyl. Compound 1 , R = 3‐pyridyl, requires two equivalents of ZnCl 2 for catalysis and reacts stereochemically in the opposite fashion. This reaction can be used to obtain enantiomerically pure ( S )‐coniine and ( S )‐anabasine.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research