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Highly regioselective ring opening of epoxides and aziridines using cerium(III) chloride

✍ Scribed by Gowravaram Sabitha; R Satheesh Babu; M Rajkumar; Ch.Srinivas Reddy; J.S Yadav

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
104 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A wide variety of epoxides and aziridines were converted to the corresponding b-halohydrins and b-haloamines using cerium(III) chloride and the cerium(III) chloride/NaI system in acetonitrile. The reactions were highly regioselective and efficient with excellent yields under mild and neutral reaction conditions.

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ChemInform Abstract: Highly Regioselecti
ChemInform Abstract: Highly Regioselective Ring Opening of Epoxides and Aziridines Using Cerium(III) Chloride.
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The regioselectivity of nucleophilic ring opening of some 3,4-epoxy and 3,4-aziridino alcohols has been studied. The nucleophiles chosen were complex hydrides (LiAIH4, Red-Al and DIBAL) and Lipshutz-or Gilman-type organocuprate reagents. The C-4 substituent in the substrates was varied in order to s