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. Author manuscript; available in PMC: 2010 Jan 12.
Published in final edited form as: Chem Soc Rev. 2009 Sep 16;38(11):3175–3192. doi: 10.1039/b816697h

Table 3.

Effect of Methyl Substitution on the Regioselectivity of Epoxide Opening under Various Conditions.

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conditions and regioselectivity (endo:exo)
epoxy alcohol R1 R2 Cs2CO3, MeOH CSA, CH2Cl2 BF3•OEt2, CH2Cl2 H2O
36 H H 1 :2.7 1 : 1.2 1.4 : 1 10 : 1
56 Me H 3.0 : 1 1 : 5.2 1 : 11 4.9 : 1
59 H Me 1 : 17 5.8 : 1 >20 : 1 >20 : 1