期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 16, 页码 6574-6583出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo2008719
关键词
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资金
- University of Alberta
- Natural Sciences and Engineering Research Council of Canada (NSERC)
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 alpha-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.
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