Tetrahedron Letters p. 5007 - 5010 (1993)
Update date:2022-08-05
Topics:
Bueno, Ana B.
Carmen Carreno
Garcia Ruano, Jose L.
Epoxidation of 2-p-tolylsulfonyl-2-cyclohexenol 3 and its OAC (4) and OMOM (5) derivatives with LiOOt-Bu and NaOOH/H2O with high stereoselectivity to give the syn epoxy alcohols 7-9. The O-triisopropylsilyl derivative (OTIPS, 6) evolves into a 63:37 mixture of syn:anti epoxides. A rationalization of these results, based on the conformational preferences of the starting substrates, is proposed.
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Doi:10.1016/0040-4039(90)80029-L
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(1993)
