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Towards the Synthesis of 3‐Silapiperidines
Author(s) -
Blaszykowski Christophe,
Brancour Célia,
Dhimane AnneLise,
Fensterbank Louis,
Malacria Max
Publication year - 2009
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.200801197
Subject(s) - chemistry , nucleophilic substitution , chloride , nucleophile , substitution reaction , combinatorial chemistry , key (lock) , total synthesis , stereochemistry , organic chemistry , catalysis , ecology , biology
A straightforward and unprecedented method towards the synthesis of 3‐silapiperidines is described. The key step involves a formal double nucleophilic substitution reaction between the (bromomethyl)dimethylsilyl chloride and a N , C ‐sp 2 ‐ 1,4‐dianionic species generated from N ‐monoprotected allylamines. Subsequent functionalizations are also presented.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)