Control of Selectivity and Reactivity of Hypervalent Iodine

2016 Fiscal Year Final Research Report

• Project/Area Number: 26410057
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: University of Hyogo
• Principal Investigator: Fujita Morifumi 兵庫県立大学, 物質理学研究科, 准教授 (00275314)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 超原子価ヨウ素 / 不斉合成 / 酸化反応

Outline of Final Research Achievements

Oxidative 1,2-difunctinalization of alkene with hypervalent iodine reagent offers a powerful strategy for constructing diverse molecular complexity, because a wide range of functional groups, such as oxygen, nitrogen, halogen, and sulfur nucleophiles, is incorporated into the C=C of alkene substrates. Compared to the most often reported carbon-heteroatom bond forming processes, the scope of oxidative carbon-carbon bond formation is still limited.
We found that enantioselective oxyarylation of (E)-6-aryl-1-silyloxyhex-3-ene and aminoarylation of N-sulfonyl-6-phenylhex-3-en-1-amine proceeded with high enantioselectivity. The silyloxy group does not act as a protection group, however, it preferentially promotes the nucleophilic oxycyclization. The aminoarylation provides hexahydrobenz[e]indoles, which are candidates of an agonist/antagonist for dopamine and serotonin receptors.

Free Research Field

有機反応化学