Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

Barry M. Trost; Christopher A. Kalnmals; Divya Ramakrishnan; Michael C. Ryan; Rebecca W. Smaha; Sean Parkin

doi:10.1021/acs.orglett.0c00504

Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

Barry M. Trost, Christopher A. Kalnmals, Divya Ramakrishnan, Michael C. Ryan, Rebecca W. Smaha, Sean Parkin

Chemistry

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

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)₃PF₆ 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.

Original language	English
Pages (from-to)	2584-2589
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.0c00504
State	Published - Apr 3 2020

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Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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)3PF6 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.",

author = "Trost, {Barry M.} and Kalnmals, {Christopher A.} and Divya Ramakrishnan and Ryan, {Michael C.} and Smaha, {Rebecca W.} and Sean Parkin",

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doi = "10.1021/acs.orglett.0c00504",

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AU - Trost, Barry M.

AU - Kalnmals, Christopher A.

AU - Ramakrishnan, Divya

AU - Ryan, Michael C.

AU - Smaha, Rebecca W.

AU - Parkin, Sean

PY - 2020/4/3

Y1 - 2020/4/3

N2 - 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)3PF6 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.

AB - 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)3PF6 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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SP - 2584

EP - 2589

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

Abstract

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