
TY  - JOUR
A1  - Schiesser, Carl H. 
A1  - Skidmore, Melissa A. 
A1  - White, Jonathan M. 
T1  - Stannanes from Cholic Acid as Enantioselective Free-Radical Reducing Agents
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2001
VL  - 54
IS  - 3
SP  - 199
EP  - 204
KW  - 
UR  - https://doi.org/10.1071/CH01045 
N2  - 7&#945;-(Dimethylstannyl)-24-nor-5&#946;-cholane (12) and 3&#946;-(dimethylstannyl)-24-nor-5&#946;-cholane (11) have been prepared from cholic and lithocholic acid, respectively, as free-radical reducing agents. Limited enantioselectivity-testing data indicate that these compounds show promise as enantioselective free-radical reducing agents. For example, reaction of ethyl (rac)-2-bromo-2-cyclopentyl-2-phenylacetate with one equivalent of either (11) or (12) in the presence of one equivalent of (S,S)-(&#8211;)-N,N&#8217;-bis(3,5-di-tert-butylsalycidene)-1,2-cyclohexanediaminomanganese(III) chloride (7) in toluene at &#8211;78&#x02DA;C provides ethyl (S)-2-cyclopentyl-2-phenylacetate, obtained with 62 and 90% ee, respectively. 
ER  -

