Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes†,Chemical Science

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Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes†
Chemical Science ( IF 9.969 ) Pub Date : 2023-02-15 , DOI: 10.1039/c9sc05111b
Leslie A. Nickerson, Benjamin D. Bergstrom, Mingchun Gao, Yuan-Shin Shiue, Croix J. Laconsay, Matthew R. Culberson, Walker A. Knauss, James C. Fettinger, Dean J. Tantillo, Jared T. Shaw

Reports of C–H insertions forming six-membered rings containing heteroatoms are rare due to Stevens rearrangements occurring after nucleophilic attack on the carbene by a heteroatom. Using donor/donor carbenes and Rh₂(R-PTAD)₄ as a catalyst, we have synthesized a collection of isochroman substrates in good yield, with excellent diastereo- and enantioselectivity, and no rearrangement products were observed. Furthermore, we report the first synthesis of six-membered rings containing nitrogen by C–H insertion to form tetrahydroisoquinolines. In one case, a Stevens rearrangement product was isolated at elevated temperature from a carbamate-protected amine substrate and computational evidence suggests formation through a free ylide not bound to rhodium.

更新日期：2020-01-02

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