Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation: Via intramolecular Friedel-Crafts alkylation

Veeranjaneyulu Lanke; Fa-Guang Zhang; Alexander Kaushansky; Ilan Marek

doi:10.1039/c9sc03832a

Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation: Via intramolecular Friedel-Crafts alkylation

Veeranjaneyulu Lanke
, Fa-Guang Zhang
, Alexander Kaushansky
, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

We herein disclose a diastereoselective ring opening of non-donor-acceptor cyclopropanes via an intramolecular Friedel-Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.

Original language	English GB
Pages (from-to)	9548-9554
Number of pages	7
Journal	Chemical Science
Volume	10
Issue number	41
DOIs	https://doi.org/10.1039/c9sc03832a
State	Published - 7 Nov 2019

ASJC Scopus subject areas

General Chemistry

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10.1039/c9sc03832a

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title = "Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation: Via intramolecular Friedel-Crafts alkylation",

abstract = "We herein disclose a diastereoselective ring opening of non-donor-acceptor cyclopropanes via an intramolecular Friedel-Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.",

author = "Veeranjaneyulu Lanke and Fa-Guang Zhang and Alexander Kaushansky and Ilan Marek",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

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doi = "10.1039/c9sc03832a",

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T1 - Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation

T2 - Via intramolecular Friedel-Crafts alkylation

AU - Lanke, Veeranjaneyulu

AU - Zhang, Fa-Guang

AU - Kaushansky, Alexander

AU - Marek, Ilan

PY - 2019/11/7

Y1 - 2019/11/7

N2 - We herein disclose a diastereoselective ring opening of non-donor-acceptor cyclopropanes via an intramolecular Friedel-Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.

AB - We herein disclose a diastereoselective ring opening of non-donor-acceptor cyclopropanes via an intramolecular Friedel-Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.

UR - https://www.scopus.com/pages/publications/85074225326

U2 - 10.1039/c9sc03832a

DO - 10.1039/c9sc03832a

M3 - مقالة

SN - 2041-6520

VL - 10

SP - 9548

EP - 9554

JO - Chemical Science

JF - Chemical Science

IS - 41

ER -

Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation: Via intramolecular Friedel-Crafts alkylation

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