Tetrahedron Letters p. 1501 - 1504 (1998)
Update date:2022-08-17
Topics:
Lautens, Mark
Fillion, Eric
Sampat, Michael
Unsymmetrical 8-oxa-3-thiabicyclo[3.2.1]octane and 9-oxa-3-thiabicyclo[3.3.1]nonane underwent highly regioselective base-induced elimination but low selectivity was observed for the sulfonyl and the aza-oxa systems. A correlation between the regioselectivity of the reaction and the proton undergoing abstraction (i.e. equatorial vs. the axial proton) was made.
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