期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 34, 页码 11884-11886出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja104956s
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资金
- National Institutes of Health [NIH GM-082935]
- National Science Foundation [NSF-0847108]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0847108] Funding Source: National Science Foundation
The catalytic enantioselective allylation of aldehydes is a long-standing problem of considerable interest to the chemical community. We disclose a new high-yielding and highly enantioselective chiral Bronsted acid-catalyzed allylboration of aldehydes. The reaction is shown to be highly general, with a broad substrate scope that covers aryl, heteroaryl, alpha,beta-unsaturated, and aliphatic aldehydes. The reaction conditions are also shown to be effective for the catalytic enantioselective crotylation of aldehydes. We believe that the high reactivity of the allylboronate is due to protonation of the boronate oxygen by the chiral phosphoric acid catalyst.
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