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Stereospecific cycloaddition of heterocumulenes to oxiranes catalyzed by organotin halide complexes
Author(s) -
Baba Akio,
Seki Kenji,
Matsuda Haruo
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270714
Subject(s) - chemistry , cycloaddition , stereospecificity , halide , ring (chemistry) , catalysis , organic chemistry , medicinal chemistry
Stereospecific cycloaddition of 2,3‐disubstituted oxiranes to heterocumulenes, including carbodiimides, isocyanates and carbon dioxide, is catalytically promoted by dialkyltin diiodide‐hexamethylphosphoric triamide (HMPA) system, producing various five‐membered heterocycles, where the configuration of the carbons in the oxirane ring is retained. In particular, the addition of isocyanates to oxiranes gave stereo‐specifically two types of products, dioxolan‐2‐imines and oxazolidin‐2‐ones independently, while the rearrangement of the former to the latter product has been already proposed.