In:
Angewandte Chemie International Edition, Wiley, Vol. 62, No. 1 ( 2023-01-02)
Abstract:
Chiral perhydroindoles are found in a number of natural products and biologically active compounds. Therefore, the development of new asymmetric methodology for rapid access to this core is of high importance. Herein, we reported a highly regio‐ and diastereo‐selective palladium/PC‐Phos‐catalyzed asymmetric Heck/Tsuji–Trost reactions of readily available amino tethered 1,3‐cyclohexadienes with aryl and alkenyl halides, delivering various functionalized chiral hexahydroindoles in good yields with high enantioselectivity. The application of this reaction to the concise synthesis of (−)‐α‐Lycorane was demonstrated. DFT computation results indicate that the difference in Δ E dis of two migration insertion transition states determines the enantioselectivity of the reaction.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202215407
Language:
English
Publisher:
Wiley
Publication Date:
2023
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7
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