ORGN 421 |
| Densely functionalized allenylic alcohols are important synthetic intermediates and targets. These compounds cannot be prepared using an aldol reaction because 1 will react with aldehydes to give the kinetically favored adduct 2 rather than the desired allene 3. In the presence of TBAF, propargyl 1 reacts with aldehydes to produce the thermodynamically more stable 3 exclusively. The same product can be obtained by treating 2 with TBAF in high yields. The high selectivity may be due to the ability of TBAF to mediate the retroaldol reaction of product 2.
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New Reactions and Methodology
1:00 PM-5:20 PM, Tuesday, 12 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
