Journal
ORGANIC LETTERS
Volume 22, Issue 7, Pages 2584-2589Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00504
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Funding
- Tamaki Foundation
- Chugai Pharmaceuticals
- National Science Foundation [ECCS-1542152]
- Stanford Chemistry
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A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu-(MeCN)(3)PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.
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