Regio- and Stereospecific Hydrative Cloke-Wilson Rearrangement

Haoran Wang; Sunewang R. Wang

doi:10.1021/acs.orglett.3c03439

Regio- and Stereospecific Hydrative Cloke-Wilson Rearrangement

Haoran Wang, Sunewang R. Wang

School of Chemistry and Molecular Engineering

East China Normal University

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

9 Scopus citations

Abstract

The Cloke-Wilson rearrangement of unsymmetrical β-diketone-derived cyclopropanes inevitably yields a mixture of two 4-acylated 2,3-dihydrofuran regiomers. By using alkynes as masked acyls, Tf₂NH-promoted Cloke-Wilson rearrangement of polysubstituted 1-(1-alkynyl)cyclopropyl ketones followed by alkyne hydration is described, regioselectively affording 2,3-dihydrofurans bearing 4-acyls nonequivalent to that involved in the Cloke-Wilson rearrangement. The 2,3-dihydrofuran rings with cis 2,3-diaryls are unexpectedly more stable than their trans diastereomers under the reaction conditions, guaranteeing the regiospecificity of this hydrative Cloke-Wilson rearrangement with high fidelity.

Original language	English
Pages (from-to)	8356-8360
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	46
DOIs	https://doi.org/10.1021/acs.orglett.3c03439
State	Published - 24 Nov 2023

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title = "Regio- and Stereospecific Hydrative Cloke-Wilson Rearrangement",

abstract = "The Cloke-Wilson rearrangement of unsymmetrical β-diketone-derived cyclopropanes inevitably yields a mixture of two 4-acylated 2,3-dihydrofuran regiomers. By using alkynes as masked acyls, Tf2NH-promoted Cloke-Wilson rearrangement of polysubstituted 1-(1-alkynyl)cyclopropyl ketones followed by alkyne hydration is described, regioselectively affording 2,3-dihydrofurans bearing 4-acyls nonequivalent to that involved in the Cloke-Wilson rearrangement. The 2,3-dihydrofuran rings with cis 2,3-diaryls are unexpectedly more stable than their trans diastereomers under the reaction conditions, guaranteeing the regiospecificity of this hydrative Cloke-Wilson rearrangement with high fidelity.",

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T1 - Regio- and Stereospecific Hydrative Cloke-Wilson Rearrangement

AU - Wang, Haoran

AU - Wang, Sunewang R.

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N2 - The Cloke-Wilson rearrangement of unsymmetrical β-diketone-derived cyclopropanes inevitably yields a mixture of two 4-acylated 2,3-dihydrofuran regiomers. By using alkynes as masked acyls, Tf2NH-promoted Cloke-Wilson rearrangement of polysubstituted 1-(1-alkynyl)cyclopropyl ketones followed by alkyne hydration is described, regioselectively affording 2,3-dihydrofurans bearing 4-acyls nonequivalent to that involved in the Cloke-Wilson rearrangement. The 2,3-dihydrofuran rings with cis 2,3-diaryls are unexpectedly more stable than their trans diastereomers under the reaction conditions, guaranteeing the regiospecificity of this hydrative Cloke-Wilson rearrangement with high fidelity.

AB - The Cloke-Wilson rearrangement of unsymmetrical β-diketone-derived cyclopropanes inevitably yields a mixture of two 4-acylated 2,3-dihydrofuran regiomers. By using alkynes as masked acyls, Tf2NH-promoted Cloke-Wilson rearrangement of polysubstituted 1-(1-alkynyl)cyclopropyl ketones followed by alkyne hydration is described, regioselectively affording 2,3-dihydrofurans bearing 4-acyls nonequivalent to that involved in the Cloke-Wilson rearrangement. The 2,3-dihydrofuran rings with cis 2,3-diaryls are unexpectedly more stable than their trans diastereomers under the reaction conditions, guaranteeing the regiospecificity of this hydrative Cloke-Wilson rearrangement with high fidelity.

UR - https://www.scopus.com/pages/publications/85179393900

U2 - 10.1021/acs.orglett.3c03439

DO - 10.1021/acs.orglett.3c03439

M3 - 文章

AN - SCOPUS:85179393900

SN - 1523-7060

VL - 25

SP - 8356

EP - 8360

JO - Organic Letters

JF - Organic Letters

IS - 46

ER -

Regio- and Stereospecific Hydrative Cloke-Wilson Rearrangement

Abstract

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