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Clemmensen reduction. Part 5. Chiral ?-hydroxy-ketones

✍ Scribed by Davis, Brian R.; Rewcastle, Gordon W.; Stevenson, Ralph J.; Woodgate, Paul D.


Book ID
120617528
Publisher
Royal Society of Chemistry
Year
1977
Weight
767 KB
Volume
19
Category
Article
ISSN
1472-7781

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A new system for catalytic enantioselect
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The reduction of a variety of achiral ketones with catecholborane as stoichiometric reductant and 0.1 equiv of oxaxaborolidine 2 as catalyst in toluene at -78'C proceeds in > 95% yield and with enantioselectivities in the range 30: 1 to 9: 1, depending on substrate. This reduction procedure is espec