Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

Ming Chang P. Yeh; Chia Jung Liang; Cheng Yuan Liu; Ya Fon Shih; I. Chen Lee; Hsiang Fang Liu; Jeng Long Wang

doi:10.1039/c3ob27352k

Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

Ming Chang P. Yeh^*, Chia Jung Liang, Cheng Yuan Liu, Ya Fon Shih, I. Chen Lee, Hsiang Fang Liu, Jeng Long Wang

^*Corresponding author for this work

Department of Chemistry

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

3 Citations (Scopus)

Abstract

Spirolactones, spirotetrahydrofurans, and spiropyrrolidines containing a vicinal cis-diol adjacent to the spiro-carbon center are prepared by one-pot epoxidation/spirocyclization of cyclohex-2-en-1-ols bearing an ester, alcohol, or amide functional side chain at the C(3) position of the ring.

Original language	English
Pages (from-to)	3393-3399
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	20
DOIs	https://doi.org/10.1039/c3ob27352k
Publication status	Published - 2013 May 28

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c3ob27352k

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title = "Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols",

abstract = "Spirolactones, spirotetrahydrofurans, and spiropyrrolidines containing a vicinal cis-diol adjacent to the spiro-carbon center are prepared by one-pot epoxidation/spirocyclization of cyclohex-2-en-1-ols bearing an ester, alcohol, or amide functional side chain at the C(3) position of the ring.",

author = "Yeh, {Ming Chang P.} and Liang, {Chia Jung} and Liu, {Cheng Yuan} and Shih, {Ya Fon} and Lee, {I. Chen} and Liu, {Hsiang Fang} and Wang, {Jeng Long}",

year = "2013",

month = may,

day = "28",

doi = "10.1039/c3ob27352k",

language = "English",

volume = "11",

pages = "3393--3399",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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T1 - Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

AU - Yeh, Ming Chang P.

AU - Liang, Chia Jung

AU - Liu, Cheng Yuan

AU - Shih, Ya Fon

AU - Lee, I. Chen

AU - Liu, Hsiang Fang

AU - Wang, Jeng Long

PY - 2013/5/28

Y1 - 2013/5/28

N2 - Spirolactones, spirotetrahydrofurans, and spiropyrrolidines containing a vicinal cis-diol adjacent to the spiro-carbon center are prepared by one-pot epoxidation/spirocyclization of cyclohex-2-en-1-ols bearing an ester, alcohol, or amide functional side chain at the C(3) position of the ring.

AB - Spirolactones, spirotetrahydrofurans, and spiropyrrolidines containing a vicinal cis-diol adjacent to the spiro-carbon center are prepared by one-pot epoxidation/spirocyclization of cyclohex-2-en-1-ols bearing an ester, alcohol, or amide functional side chain at the C(3) position of the ring.

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UR - http://www.scopus.com/inward/citedby.url?scp=84877279323&partnerID=8YFLogxK

U2 - 10.1039/c3ob27352k

DO - 10.1039/c3ob27352k

M3 - Article

C2 - 23563191

AN - SCOPUS:84877279323

SN - 1477-0520

VL - 11

SP - 3393

EP - 3399

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 20

ER -

Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

Abstract

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CCDC 912990: Experimental Crystal Structure Determination

CCDC 912320: Experimental Crystal Structure Determination

CCDC 912316: Experimental Crystal Structure Determination

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Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 912990: Experimental Crystal Structure Determination

CCDC 912320: Experimental Crystal Structure Determination

CCDC 912316: Experimental Crystal Structure Determination

Cite this