Adition of 2-oxazolidinones to arylidenecyclopropanes: A highly efficient method for the preparation of GEM-aryl disubstituted homoallylic oxazolidinones

Amal I. Siriwardana; Kalum K.A.D.S. Kathriarachchi; Itaru Nakamura; Yoshinori Yamamoto

doi:10.3987/COM-05-S(K)28

Adition of 2-oxazolidinones to arylidenecyclopropanes: A highly efficient method for the preparation of GEM-aryl disubstituted homoallylic oxazolidinones

Amal I. Siriwardana^*
, Kalum K.A.D.S. Kathriarachchi
, Itaru Nakamura
, Yoshinori Yamamoto

^*Corresponding author for this work

Tohoku University

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

9 Citations (Scopus)

Abstract

The copper-catalyzed reaction of arylidenecyclopropanes (1) with 2-oxazolidinone (2) gave the corresponding homoallylic oxazolidinones (3) in good to high yields. For example, the reaction of diphenylmethylenecyclopropane (1a), {bis(p-tolyl)methylenecyclopropane (1b), and {bis(p-anisyl)methylene}-cyclopropane (1d) in the presence of 10 mol% of Cu(OTf)₂ without solvent proceeded at 120°C, giving the corresponding homoallylic oxazolidinones (3a, 3b, and 3d) in 89, 80, and 58% yields, respectively.

Original language	English
Pages (from-to)	333-339
Number of pages	7
Journal	Heterocycles
Volume	66
Issue number	1
DOIs	https://doi.org/10.3987/COM-05-S(K)28
Publication status	Published - 31 Dec 2005
Externally published	Yes

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title = "Adition of 2-oxazolidinones to arylidenecyclopropanes: A highly efficient method for the preparation of GEM-aryl disubstituted homoallylic oxazolidinones",

abstract = "The copper-catalyzed reaction of arylidenecyclopropanes (1) with 2-oxazolidinone (2) gave the corresponding homoallylic oxazolidinones (3) in good to high yields. For example, the reaction of diphenylmethylenecyclopropane (1a), \{bis(p-tolyl)methylenecyclopropane (1b), and \{bis(p-anisyl)methylene\}-cyclopropane (1d) in the presence of 10 mol\% of Cu(OTf)2 without solvent proceeded at 120°C, giving the corresponding homoallylic oxazolidinones (3a, 3b, and 3d) in 89, 80, and 58\% yields, respectively.",

author = "Siriwardana, \{Amal I.\} and Kathriarachchi, \{Kalum K.A.D.S.\} and Itaru Nakamura and Yoshinori Yamamoto",

year = "2005",

month = dec,

day = "31",

doi = "10.3987/COM-05-S(K)28",

language = "English",

volume = "66",

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journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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T1 - Adition of 2-oxazolidinones to arylidenecyclopropanes

T2 - A highly efficient method for the preparation of GEM-aryl disubstituted homoallylic oxazolidinones

AU - Siriwardana, Amal I.

AU - Kathriarachchi, Kalum K.A.D.S.

AU - Nakamura, Itaru

AU - Yamamoto, Yoshinori

PY - 2005/12/31

Y1 - 2005/12/31

N2 - The copper-catalyzed reaction of arylidenecyclopropanes (1) with 2-oxazolidinone (2) gave the corresponding homoallylic oxazolidinones (3) in good to high yields. For example, the reaction of diphenylmethylenecyclopropane (1a), {bis(p-tolyl)methylenecyclopropane (1b), and {bis(p-anisyl)methylene}-cyclopropane (1d) in the presence of 10 mol% of Cu(OTf)2 without solvent proceeded at 120°C, giving the corresponding homoallylic oxazolidinones (3a, 3b, and 3d) in 89, 80, and 58% yields, respectively.

AB - The copper-catalyzed reaction of arylidenecyclopropanes (1) with 2-oxazolidinone (2) gave the corresponding homoallylic oxazolidinones (3) in good to high yields. For example, the reaction of diphenylmethylenecyclopropane (1a), {bis(p-tolyl)methylenecyclopropane (1b), and {bis(p-anisyl)methylene}-cyclopropane (1d) in the presence of 10 mol% of Cu(OTf)2 without solvent proceeded at 120°C, giving the corresponding homoallylic oxazolidinones (3a, 3b, and 3d) in 89, 80, and 58% yields, respectively.

UR - https://www.scopus.com/pages/publications/33646877876

U2 - 10.3987/COM-05-S(K)28

DO - 10.3987/COM-05-S(K)28

M3 - Article

AN - SCOPUS:33646877876

SN - 0385-5414

VL - 66

SP - 333

EP - 339

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Adition of 2-oxazolidinones to arylidenecyclopropanes: A highly efficient method for the preparation of GEM-aryl disubstituted homoallylic oxazolidinones

Abstract

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