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Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

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Abstract

Described herein is the Brønsted acid-catalyzed double C(sp3)–H bond functionalization of alkyl phenethyl ether derivatives. In this process, a [1,5]-[1,5]-hydride shift occurred successively to afford tricyclic fused pyran derivatives in excellent chemical yields with excellent diastereoselectivities (up to >20 : 1). The key to achieve this reaction was the introduction of two methyl groups at the benzylic position, which was effective in both hydride shift processes: (1) the Thorpe–Ingold effect for the first hydride shift and (2) conformational control in the second hydride shift.

Graphical abstract: Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

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Publication details

The article was received on 12 May 2018, accepted on 23 Jun 2018 and first published on 25 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC02103A
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

    K. Mori, N. Umehara and T. Akiyama, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC02103A

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