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Stereocontrolled Addition of Some Sulphenyl Halydes to Bicyclohept-2-en-6-ones and Modification of the Adducts
Bigg, Martin G.,Roberts, Stanley M.,Suschitzky, Hans
, p. 926 - 929 (2007/10/02)
The bicycloheptenones (1) and (2) reacted with the sulphenyl chlorides (13)-(15) in a highly regioselective manner to give the corresponding adducts (3)-(8) on 77-92percent yield. m-Chloroperoxybenzoic acid oxidation of the ketone (5) led to products (9), (10), and (23) resulting from oxidation at sulphur and/or Bayer-Villiger ring expansion.The corresponding dichloroketone (8) suffers oxidation at sulphur only to give the sulphoxide (11) and the sulphone (12).The 7,7-dichlorobicyclohept-6-one (8) yielded tetra-substituted cyclopentane derivatives (18)-(21) of defined stereochemistry on addition of methanol or piperidine across the C6-C7 bond
