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. Author manuscript; available in PMC: 2015 Sep 29.
Published in final edited form as: J Am Chem Soc. 2015 May 18;137(21):6941–6946. doi: 10.1021/jacs.5b03570

Table 4.

Proximal-methyl (E)-trisubstituted epoxy alcohols cyclizations under [Rh(CO)2Cl]2 and (±)-CSA promotion

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entry substrate activator 7: 8 yield 7 (%)a
1 6e, n = 0 [Rh(CO)2Cl]2b 12: 1 81
2 6e, n = 0 (±)-CSAc   1: >20 –
3 6f, n = 1 [Rh(CO)2Cl]2d   4: 1 21
4 6f, n = 1 (±)-CSAe   1: >20 –
a

Isolated yield.

b

[Rh(CO)2Cl]2 (10 mol %), 1,4-Dioxane, 80 °C.

c

(±)-CSA (10 mol %), CH2Cl2, rt.

d

[Rh(CO)2Cl]2 (10 mol %), THF, 60 °C.

e

(±)-CSA (100 mol %), CH2Cl2, rt.