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
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

All Science Journal Classification (ASJC) codes

General Chemistry

Access to Document

10.1039/c9sc03832a

Cite this

@article{d61be9c118aa437c820ac067aaa0b88e,

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.",

year = "2019",

month = nov,

day = "7",

doi = "10.1039/c9sc03832a",

language = "الإنجليزيّة",

volume = "10",

pages = "9548--9554",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "41",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=85074225326&partnerID=8YFLogxK

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this