Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
J Org Chem. 2011 Aug 19;76(16):6574-83. doi: 10.1021/jo2008719. Epub 2011 Jul 25.
The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to α-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.
手性炔烃与醛的对映选择性加成反应被提出，包括首例不对称三炔加成反应的例子。对 Carreira 炔基化反应条件的修饰表明，二炔和三炔与α-支链醛的加成反应在短短 4 小时内即可完全进行，并且这些反应对所测试的二炔和三炔（芳基、烷基和硅基）具有良好的收率和对映选择性（最高达 98%ee）。有两个例子（20 和 24）表明，这种不对称加成反应的产物可以在不影响对映体纯度的情况下进行进一步的操作（脱硅和三唑形成）。
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