Enantioselective Desymmetrization Triggered by Iminium-Enamine Activation: Access to Complex Cyclohepta[b]indoles.

Autor: Magham LR; Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad, 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201 002, India., Thopate SB; Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad, 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201 002, India., Samad A; Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad, 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201 002, India., Chegondi R; Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad, 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201 002, India.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Mar 13; Vol. 29 (15), pp. e202203435. Date of Electronic Publication: 2023 Feb 08.
DOI: 10.1002/chem.202203435
Abstrakt: The expeditious construction of complex molecules having multiple stereocentres is highly desirable in organic chemistry. In the present communication, we report the development of an organocatalytic asymmetric desymmetrization of prochiral enal-tethered cyclohexadienones via the C3-selective Friedel-Crafts alkylation of indoles triggered by LUMO-lowering iminium activation/HOMO-raising enamine activation. The reaction provides access to bicyclic enones, which further undergo acid-mediated intramolecular annulation from C2-position to afford highly strained cyclohepta[b]indoles with five contiguous stereocentres and three new C-C bonds in excellent enantioselectivity and diastereoselectivity.
(© 2022 Wiley-VCH GmbH.)
Databáze: MEDLINE
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