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. Author manuscript; available in PMC: 2010 Jun 24.
Published in final edited form as: J Am Chem Soc. 2009 Jun 24;131(24):8434–8445. doi: 10.1021/ja809821x

Table 5.

Diastereoselective Synthesis of α-Methyl Substituted Allylic Alcohols

graphic file with name nihms120473f16.jpg
entry R1 R2 RCHO yield (%) dra product major product
1 n-Bu Cl graphic file with name nihms120473t20.jpg 68 >20:1 41 graphic file with name nihms120473t21.jpg
2 (CH2)3Cl Cl 67 >20:1 42
3 (CH2)2OTBDPS Cl 78 >20:1 43
4 n-Bu Me 78 >20:1 41
5 (CH2)2OTBDPS Me 75 >20:1 43
6 n-Bu Cl graphic file with name nihms120473t22.jpg 51 >20:1 44 graphic file with name nihms120473t23.jpg
7 (CH2)2OTBDPS Cl 57 17:1 45
8 n-Bu Br graphic file with name nihms120473t24.jpg 70 17:1 46 graphic file with name nihms120473t25.jpg
9 CH2OTBDPS Br 63 9–13:1 47
10 (CH2)2OTBDPS Br 59 11:1 48
11 (CH2)2OTBDPS Cl graphic file with name nihms120473t26.jpg 47 >20:1 49 graphic file with name nihms120473t27.jpg
12 (CH2)2OTBDPS Cl graphic file with name nihms120473t28.jpg 55 1:4 50 graphic file with name nihms120473t29.jpg
a

Diastereomeric ratio (anti-Felkin : Felkin) based on 1H NMR of crude product. Relative stereochemistry was determined by X-ray crystallography, Mosher ester analysis, or Heathcock’s analysis. See Supporting Information for details.