Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 26, Pages 9134-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja809610h
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- NIGMS NIH HHS [GM-59417, R01 GM059417, R01 GM059417-10] Funding Source: Medline
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Asymmetric 1,4-dihydroxytations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B-2(pin)(2)) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyctic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereosetective carbonyl allylation with the intermediate bis(boronate) ester is also described.
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