Chiral Induction in Aryl Radical Cyclization to the Aldimino Functional Group

DOI: 10.1039/c39930000966

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 966 - 968 (1993)

Update date:2022-07-29

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Authors:

Tomaszewski, Miroslaw J.

Warkentin, John

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Article abstract of DOI:10.1039/c39930000966

6-endo Cyclization of aryl radicals to carbon of aldimino double bonds (N-5/C-6) in chiral ortho-substituents afforded 1,2,3,4-tetrahydroisoquinolines in yields to 69percent, with 58percent d.e. and 97percent e.e., while 5-exo cyclization to carbon in isomeric radicals (C-5/N-6 aldimine), leading to indanamines, was highly regioselective and fast, k_5-exo = 3.9 * 10⁸ s^-1 at 80 deg C.

Full text of DOI:10.1039/c39930000966

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