Tetrahedron Letters p. 387 - 390 (1999)
Update date:2022-08-11
Topics:
De Sousa
Kee
O'Brien
Watson
The stereoselectivity of m-CPBA epoxidation of diprotected cis-4,5- dihydroxycyclohexenes has been studied as a function of protecting group, solvent and in one example, epoxidising reagent. Three different ways of obtaining high levels of trans diastereoselectivity have been uncovered. In addition, the results suggest that bulky silyl protecting groups (eg triethylsilyl and tert-butyldimethylsilyl) can, in CH2Cl2, behave as moderate cis-directors via hydrogen bonding to m-CPBA.
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