Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence

Jason Hugh Chaplin, Kristal Emily Jackson, Jonathan White, Bernard Luke Flynn

Research output: Contribution to journalArticleResearchpeer-review

8 Citations (Scopus)

Abstract

Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids
Original languageEnglish
Pages (from-to)3659 - 3664
Number of pages6
JournalJournal of Organic Chemistry
Volume79
Issue number8
DOIs
Publication statusPublished - 2014

Cite this

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title = "Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence",
abstract = "Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids",
author = "Chaplin, {Jason Hugh} and Jackson, {Kristal Emily} and Jonathan White and Flynn, {Bernard Luke}",
year = "2014",
doi = "10.1021/jo500040b",
language = "English",
volume = "79",
pages = "3659 -- 3664",
journal = "Journal of Organic Chemistry",
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publisher = "American Chemical Society",
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Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence. / Chaplin, Jason Hugh; Jackson, Kristal Emily; White, Jonathan; Flynn, Bernard Luke.

In: Journal of Organic Chemistry, Vol. 79, No. 8, 2014, p. 3659 - 3664.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence

AU - Chaplin, Jason Hugh

AU - Jackson, Kristal Emily

AU - White, Jonathan

AU - Flynn, Bernard Luke

PY - 2014

Y1 - 2014

N2 - Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids

AB - Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids

UR - http://pubs.acs.org/doi/pdf/10.1021/jo500040b

U2 - 10.1021/jo500040b

DO - 10.1021/jo500040b

M3 - Article

VL - 79

SP - 3659

EP - 3664

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -