4. Oxidações QFL-5928 - Síntese Orgânica Prof. Luiz F. Silva ... - USP
4. Oxidações QFL-5928 - Síntese Orgânica Prof. Luiz F. Silva ... - USP
4. Oxidações QFL-5928 - Síntese Orgânica Prof. Luiz F. Silva ... - USP
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<strong>4.</strong> <strong>Oxidações</strong> <strong>QFL</strong>-<strong>5928</strong> - <strong>Síntese</strong> <strong>Orgânica</strong><br />
A popular way to prepare carboxylic acids from primary alcohols is the<br />
oxidation with DMP or IBX to the corresponding aldehyde, which is then oxidized to<br />
the acid using NaClO 2 (Pinnick oxidation), as exemplified in the synthesis of (+)-<br />
azaspiracid-1 and (─)-penifulvin A.<br />
H<br />
OH<br />
1) 3 equiv IBX<br />
DMSO, rt, 20 min<br />
2) NaClO2, t-BuOH<br />
2-methyl-2-butene<br />
NaH2PO4, rt,1h<br />
92%<br />
O<br />
H<br />
<strong>Prof</strong>. <strong>Luiz</strong> F. <strong>Silva</strong> Jr - IQ-<strong>USP</strong> - 2012 20<br />
O<br />
H<br />
O<br />
H O<br />
( )-Penifulvin A<br />
Gaich and Mulzer JACS 2009, 131, 452<br />
H<br />
CO2H<br />
The oxidation of alcohols with IBX can be chemoselective. For example,<br />
after deprotection of an acetonide, an allylic alcohol was selectively oxidized.<br />
Como esta oxidação seletiva pode ser explicada?<br />
39<br />
40
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