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Enantioselective Synthesis of (+)‐α‐Conhydrine and (–)‐Sedamine by L ‐Proline‐Catalysed α‐Aminooxylation
Author(s) -
Shaikh Tanveer Mahamadali,
Sudalai Arumugam
Publication year - 2010
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.201000169
Subject(s) - chemistry , piperidine , enantioselective synthesis , proline , organocatalysis , intramolecular force , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , amino acid , biochemistry
An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)‐α‐conhydrine (98 % ee ) and (–)‐sedamine (95 % ee ), by L ‐proline‐catalysed α‐aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.