Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

Ming Chang P. Yeh; Chia Jung Liang; Chern Wei Fan; Wei Hang Chiu; Jun Yuan Lo

doi:10.1021/jo301764g

Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

Ming Chang P. Yeh^*
, Chia Jung Liang
, Chern Wei Fan
, Wei Hang Chiu
, Jun Yuan Lo

^*Corresponding author for this work

Department of Chemistry

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

21 Citations (Scopus)

Abstract

The FeCl₃-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3- arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl- protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

Original language	English
Pages (from-to)	9707-9717
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	77
Issue number	21
DOIs	https://doi.org/10.1021/jo301764g
Publication status	Published - 2012 Nov 2

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo301764g

Cite this

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title = "Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols",

abstract = "The FeCl3-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3- arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl- protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.",

author = "Yeh, \{Ming Chang P.\} and Liang, \{Chia Jung\} and Fan, \{Chern Wei\} and Chiu, \{Wei Hang\} and Lo, \{Jun Yuan\}",

year = "2012",

month = nov,

day = "2",

doi = "10.1021/jo301764g",

language = "English",

volume = "77",

pages = "9707--9717",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

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TY - JOUR

T1 - Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

AU - Yeh, Ming Chang P.

AU - Liang, Chia Jung

AU - Fan, Chern Wei

AU - Chiu, Wei Hang

AU - Lo, Jun Yuan

PY - 2012/11/2

Y1 - 2012/11/2

N2 - The FeCl3-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3- arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl- protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

AB - The FeCl3-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3- arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl- protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

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U2 - 10.1021/jo301764g

DO - 10.1021/jo301764g

M3 - Article

C2 - 23075326

AN - SCOPUS:84868359352

SN - 0022-3263

VL - 77

SP - 9707

EP - 9717

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

Abstract

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CCDC 965393: Experimental Crystal Structure Determination

CCDC 965398: Experimental Crystal Structure Determination

CCDC 965394: Experimental Crystal Structure Determination

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Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 965393: Experimental Crystal Structure Determination

CCDC 965398: Experimental Crystal Structure Determination

CCDC 965394: Experimental Crystal Structure Determination

Cite this