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syn ‐Allylstannation of N ‐Acyliminium Intermediates by Tributyl[γ‐(silyloxy)allyl]stannanes: A Key Reaction for the Diastereoselective Synthesis of Polyhydroxypiperidines and Polyhydroxyazepanes
Author(s) -
Chevallier Floris,
Lumbroso Alexandre,
Beaudet Isabelle,
Le Grognec Erwan,
Toupet Loïc,
Quintard JeanPaul
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.201100302
Subject(s) - chemistry , dihydroxylation , stereoselectivity , adduct , metathesis , ring closing metathesis , stereochemistry , selectivity , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , polymer , polymerization
The allylstannation of N ‐alkenyl N ‐acyliminium intermediates by tributyl[γ‐(silyloxy)allyl]stannanes afforded the expected adducts with a high syn ‐selectivity (up to 99:1). Ensuing ring‐closing metathesis afforded dehydropiperidines or dehydroazepanes which were engaged in a stereoselective dihydroxylation reaction leading to polyhydroxypiperidines or polyhydroxyazepanes in good yields. This sequence was applied to a diastereoselective synthesis of (±)‐1‐deoxy‐gulonojirimycine.