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Regioselective epoxide ring opening. Steroselective synthesis of a tetrahydropyran ring
Author(s) -
Gruttadauria Michelangelo,
Noto Renato,
Riela Serena
Publication year - 1998
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.5570350414
Subject(s) - tetrahydropyran , chemistry , regioselectivity , stereoselectivity , stereocenter , epoxide , tetrahydrofuran , ring (chemistry) , stereochemistry , allylic alcohol , allylic rearrangement , organic chemistry , enantioselective synthesis , solvent , catalysis
The stereoselective synthesis of a 2‐substituted tetrahydropyran with adjacent alkoxy‐bearing stereogenic centre is described. The key steps of this synthesis were the stereoselective epoxidation of an allylic alcohol and the regioselective epoxide ring opening by lithium aluminum hydride. The regio and stereoselective synthesis of a trihydroxyselenide and a trihydroxysulfide is also described. The latter compounds are not suitable for cyclization to tetrahydrofuran ring.