Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration
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- 作者：Heather E. Burks ; Laura T. Kliman ; James P. Morken
- 刊名：Journal of the American Chemical Society
- 出版年：2009
- 出版时间：July 8, 2009
- 年：2009
- 卷：131
- 期：26
- 页码：9134-9135
- 全文大小：153K
- 年卷期：v.131,no.26(July 8, 2009)
- ISSN：1520-5126
文摘
Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B2(pin)2) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic 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, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.