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Stereoselective Synthesis of Stannylated Dehydropiperidines and Dehydroazepanes
Author(s) -
Lumbroso Alexandre,
Coeffard Vincent,
Gatineau David,
Stecko Sebastian,
Beaudet Isabelle,
Quintard JeanPaul,
Le Grognec Erwan
Publication year - 2016
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.201600903
Subject(s) - chemistry , isomerization , stereoselectivity , metathesis , ring closing metathesis , catalysis , double bond , ring (chemistry) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , polymerization , polymer
An efficient allylation and butenylation of N ‐alkoxycarbonyl‐2‐tributylstannyl‐1,3‐oxazolidines derived from ( S )‐vinylglycinol or ( S )‐styrylglycinol is described. After conversion of the stannylated azadienes into stannylated dienyl oxazolidinones, a ring‐closing metathesis generates dehydropiperidine or dehydroazepane; both are interesting scaffolds for the synthesis of polyfunctionnalized piperidines or azepanes. Whereas the dehydropiperidine synthesis was found to be selective regardless of the Grubbs catalyst used, we found that Grubbs II catalyst induced partial double bond isomerization in the dehydroazepane series. In addition, when allyltrimethylsilane was used in the ring‐opening reactions of N ‐alkoxycarbonyl‐2‐tributylstannyl‐1,3‐oxazolidines, cyclopropyl derivatives were selectively obtained.