Novel [1, N]-Carbon to Carbon Rearrangement of an Ester Group via Organotitanium Intermediates Wherein the N Varies from 2 to 5. Full Scope and Limitation Leading Predominantly to the Rearrangement

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Malonates and methanetricarboxylates having an unsaturated side chain such as <b>2</b>, <b>12</b>, <b>20</b>, <b>22</b>, <b>24</b>, <b>31</b>, or <b>37</b> underwent a new ester rearrangement reaction promoted by (<i>η</i><sup>2</sup>-propene)Ti(O-<i>i</i>-Pr)<sub>2</sub> to afford the succinate derivative <b>4</b> or <i>α</i>,<i>β</i>-unsaturated ester <b>17</b>, <b>21</b>, <b>23</b>, <b>25</b>, <b>34</b>, or <b>38</b> via the migration of the ester group from its original bis- or tris-ester position to the acetylene- or olefin-titanium complex. It has been found that the side reactions competing with the desired migration are dealkylation of the side chain of the ester and a simple cyclization. The substrates and conditions which allow the ester migration a preferential path were determined as well as the scope and limitation of this reaction.

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  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(7), 1673-1681, 1998-07-15

    The Chemical Society of Japan

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