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. Author manuscript; available in PMC: 2014 Jan 4.
Published in final edited form as: Org Lett. 2012 Dec 18;15(1):46–49. doi: 10.1021/ol303003g

Table 3.

Alkene Dioxygenation with Chiral Auxiliaries Derived from 8-Substituted Menthonea

graphic file with name nihms430353u5.jpg
substrate product yieldb drc
graphic file with name nihms430353t17.jpg
(13)		 graphic file with name nihms430353t18.jpg
(13a)		 69% 86:14
graphic file with name nihms430353t19.jpg
(14)		 graphic file with name nihms430353t20.jpg
(14a)		 70% 86:14
graphic file with name nihms430353t21.jpg
(15)		 graphic file with name nihms430353t22.jpg
(15a)		 54% 86:14
graphic file with name nihms430353t23.jpg
(16)		 graphic file with name nihms430353t24.jpg
(16a)		 44% 85:15
graphic file with name nihms430353t25.jpg
(17)		 graphic file with name nihms430353t26.jpg
(17a)		 37% 90:10
a

Conditions: substrate (1 equiv), PdCl2(PhCN)2 (0.05 equiv), PhI(OBz)2 (2–3 equiv), dry toluene (0.12 M in substrate), 50 °C, 8 h.

b

Isolated yield.

c

Determined by relative integrations of at least 2 pairs of peaks in the 13C and/or 1H NMR spectra; see Supporting Information for details.