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- Title
Direct Catalytic Asymmetric and Regiodivergent N1‐ and C3‐Allenylic Alkylation of Indoles.
- Authors
Zha, Taochun; Rui, Jiehui; Zhang, Zhihan; Zhang, Dongqiang; Yang, Zhirong; Yu, Peiyuan; Wang, Yingcheng; Peng, Fangzhi; Shao, Zhihui
- Abstract
Herein we report a Pd‐catalyzed asymmetric allenylic alkylation strategy for the direct functionalization of 1H‐indoles by employing P‐chiral BIBOP‐type ligands. The regioselectivity (N1/C3) of this process can be switched efficiently. Using Cs2CO3 at elevated temperatures in MeCN, N1‐alkylated indoles bearing axial chirality with a stereocenter non‐adjacent (β) to the nitrogen are produced in good yields with high enantioselectivity and complete N1‐regioselectivity regardless of the electronic properties and substitution patterns of diverse indoles. Using K2CO3 at room temperature in CH2Cl2, chiral C3‐alkylated indoles can also be obtained. Notably, we introduce a new class of tri‐substituted allenylic electrophiles that proceeded through different pathways from di‐substituted allenylic electrophiles.
- Subjects
CHIRALITY element; INDOLE compounds; FRIEDEL-Crafts reaction; ALKYLATION; HIGH temperatures; ELECTROPHILES; KINETIC resolution
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 21, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202300844