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. Author manuscript; available in PMC: 2010 May 13.
Published in final edited form as: J Am Chem Soc. 2009 May 13;131(18):6516–6524. doi: 10.1021/ja900147s

Table 3.

Stereoselective Synthesis of Trisubstituted α-Hydroxycyclopropyl Carbinols

graphic file with name nihms112354t23.jpg
entry cyclopropyl
boronate ester
α-hydroxy
cyclopropyl carbinol
Isolated
yield (%)a
1 graphic file with name nihms112354t24.jpg graphic file with name nihms112354t25.jpg 89b
2 graphic file with name nihms112354t26.jpg graphic file with name nihms112354t27.jpg 93b
3 graphic file with name nihms112354t28.jpg graphic file with name nihms112354t29.jpg 91
4 graphic file with name nihms112354t30.jpg graphic file with name nihms112354t31.jpg 90
5 graphic file with name nihms112354t32.jpg graphic file with name nihms112354t33.jpg 86
6 graphic file with name nihms112354t34.jpg graphic file with name nihms112354t35.jpg 88
7 graphic file with name nihms112354t36.jpg graphic file with name nihms112354t37.jpg 75b
8 graphic file with name nihms112354t38.jpg graphic file with name nihms112354t39.jpg 80
a

Only one diastereomer detected by 1H NMR.

b

Syn stereochemistry of α-hydroxycyclopropyl carbinols established by single crystal X-ray diffraction.