Highly stereoselective Friedel-Crafts alkylations of unactivated benzenes by episulfonium ion cyclizations

Bruce Branchaud, Heather S. Blanchette

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Intermolecular additions of highly enantiomerically enriched episulfonium ions onto activated benzene rings are known to accomplish chiral Friedel-Crafts alkylations. Unactivated benzenes are either unreactive or can give low stereoselectivities. Intramolecular cyclizations should be faster than intermolecular additions; thus, cyclization reactions should be able to avoid undesired episulfonium ion racemization. The work reported here tests that hypothesis and demonstrates that cyclizations of enantiomerically enriched episulfonium ions onto unactivated benzene rings are highly stereoselective.

Original languageEnglish (US)
Pages (from-to)351-353
Number of pages3
JournalTetrahedron Letters
Volume43
Issue number3
DOIs
StatePublished - Jan 14 2002
Externally publishedYes

Fingerprint

Cyclization
Alkylation
Benzene
Ions
Stereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Highly stereoselective Friedel-Crafts alkylations of unactivated benzenes by episulfonium ion cyclizations. / Branchaud, Bruce; Blanchette, Heather S.

In: Tetrahedron Letters, Vol. 43, No. 3, 14.01.2002, p. 351-353.

Research output: Contribution to journalArticle

@article{104a58d50ded416191cd8dab90ae3b26,
title = "Highly stereoselective Friedel-Crafts alkylations of unactivated benzenes by episulfonium ion cyclizations",
abstract = "Intermolecular additions of highly enantiomerically enriched episulfonium ions onto activated benzene rings are known to accomplish chiral Friedel-Crafts alkylations. Unactivated benzenes are either unreactive or can give low stereoselectivities. Intramolecular cyclizations should be faster than intermolecular additions; thus, cyclization reactions should be able to avoid undesired episulfonium ion racemization. The work reported here tests that hypothesis and demonstrates that cyclizations of enantiomerically enriched episulfonium ions onto unactivated benzene rings are highly stereoselective.",
author = "Bruce Branchaud and Blanchette, {Heather S.}",
year = "2002",
month = "1",
day = "14",
doi = "10.1016/S0040-4039(01)02173-6",
language = "English (US)",
volume = "43",
pages = "351--353",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "3",

}

TY - JOUR

T1 - Highly stereoselective Friedel-Crafts alkylations of unactivated benzenes by episulfonium ion cyclizations

AU - Branchaud, Bruce

AU - Blanchette, Heather S.

PY - 2002/1/14

Y1 - 2002/1/14

N2 - Intermolecular additions of highly enantiomerically enriched episulfonium ions onto activated benzene rings are known to accomplish chiral Friedel-Crafts alkylations. Unactivated benzenes are either unreactive or can give low stereoselectivities. Intramolecular cyclizations should be faster than intermolecular additions; thus, cyclization reactions should be able to avoid undesired episulfonium ion racemization. The work reported here tests that hypothesis and demonstrates that cyclizations of enantiomerically enriched episulfonium ions onto unactivated benzene rings are highly stereoselective.

AB - Intermolecular additions of highly enantiomerically enriched episulfonium ions onto activated benzene rings are known to accomplish chiral Friedel-Crafts alkylations. Unactivated benzenes are either unreactive or can give low stereoselectivities. Intramolecular cyclizations should be faster than intermolecular additions; thus, cyclization reactions should be able to avoid undesired episulfonium ion racemization. The work reported here tests that hypothesis and demonstrates that cyclizations of enantiomerically enriched episulfonium ions onto unactivated benzene rings are highly stereoselective.

UR - http://www.scopus.com/inward/record.url?scp=0037074131&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037074131&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)02173-6

DO - 10.1016/S0040-4039(01)02173-6

M3 - Article

VL - 43

SP - 351

EP - 353

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 3

ER -