Dearomatizing Annelation of Five-Membered Rings to Naphthalenes by Organolithium Cyclization.

Jonathan Clayden; Martin N. Kenworthy

doi:10.1021/ol0172626

Dearomatizing Annelation of Five-Membered Rings to Naphthalenes by Organolithium Cyclization.

Jonathan Clayden, Martin N. Kenworthy

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

Abstract

.gamma.-Lithiopropylnaphthalenes and their oxa- and aza-tethered analogs cyclize by nucleophilic addn. of the organolithium to the naphthalene ring. The resulting benzyllithiums react stereoselectively with electrophiles to give dearomatized tricyclic products with structural similarity to the arylnaphthalene lignans. [on SciFinder (R)]

Original language	English
Pages (from-to)	787-790
Journal	Organic Letters
Volume	4
DOIs	https://doi.org/10.1021/ol0172626
Publication status	Published - 2002

Keywords

Lignans Role: PNU (Preparation, unclassified), PREP (Preparation) (arylnaphthalene; dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization); Cyclization; Lithiation; Substitution reaction (dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization)

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10.1021/ol0172626

CCDC 182745: Experimental Crystal Structure Determination
Clayden, J. (Contributor) & Kenworthy, M. N. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2002
DOI: 10.5517/cc6450h, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6450h&sid=DataCite
Dataset

Cite this

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title = "Dearomatizing Annelation of Five-Membered Rings to Naphthalenes by Organolithium Cyclization.",

abstract = ".gamma.-Lithiopropylnaphthalenes and their oxa- and aza-tethered analogs cyclize by nucleophilic addn. of the organolithium to the naphthalene ring. The resulting benzyllithiums react stereoselectively with electrophiles to give dearomatized tricyclic products with structural similarity to the arylnaphthalene lignans. [on SciFinder (R)]",

keywords = "Lignans Role: PNU (Preparation, unclassified), PREP (Preparation) (arylnaphthalene; dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization); Cyclization; Lithiation; Substitution reaction (dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization)",

author = "Jonathan Clayden and Kenworthy, {Martin N.}",

year = "2002",

doi = "10.1021/ol0172626",

language = "English",

volume = "4",

pages = "787--790",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Dearomatizing Annelation of Five-Membered Rings to Naphthalenes by Organolithium Cyclization.

AU - Clayden, Jonathan

AU - Kenworthy, Martin N.

PY - 2002

Y1 - 2002

N2 - .gamma.-Lithiopropylnaphthalenes and their oxa- and aza-tethered analogs cyclize by nucleophilic addn. of the organolithium to the naphthalene ring. The resulting benzyllithiums react stereoselectively with electrophiles to give dearomatized tricyclic products with structural similarity to the arylnaphthalene lignans. [on SciFinder (R)]

AB - .gamma.-Lithiopropylnaphthalenes and their oxa- and aza-tethered analogs cyclize by nucleophilic addn. of the organolithium to the naphthalene ring. The resulting benzyllithiums react stereoselectively with electrophiles to give dearomatized tricyclic products with structural similarity to the arylnaphthalene lignans. [on SciFinder (R)]

KW - Lignans Role: PNU (Preparation, unclassified), PREP (Preparation) (arylnaphthalene; dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization); Cyclization; Lithiation; Substitution reaction (dearomatizing annelation of

U2 - 10.1021/ol0172626

DO - 10.1021/ol0172626

M3 - Article

SN - 1523-7052

VL - 4

SP - 787

EP - 790

JO - Organic Letters

JF - Organic Letters

ER -

Dearomatizing Annelation of Five-Membered Rings to Naphthalenes by Organolithium Cyclization.

Abstract

Keywords

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Datasets

CCDC 182745: Experimental Crystal Structure Determination

Cite this