Enantioselective Friedel-Crafts Alkylation of Furans with o-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst

Yoon Sung Cho; Seung Tae Kim; Do Hyun Ryu

doi:10.1021/acs.orglett.2c00404

Enantioselective Friedel-Crafts Alkylation of Furans with o-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst

Yoon Sung Cho
, Seung Tae Kim
, Do Hyun Ryu

Department of Chemistry

Sungkyunkwan University

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

21 Scopus citations

Abstract

A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts furan alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99%) with excellent enantioselectivity (up to >99% ee).

Original language	English
Pages (from-to)	1732-1736
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.2c00404
State	Published - 4 Mar 2022

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10.1021/acs.orglett.2c00404

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title = "Enantioselective Friedel-Crafts Alkylation of Furans with o-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst",

abstract = "A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts furan alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99\%) with excellent enantioselectivity (up to >99\% ee).",

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doi = "10.1021/acs.orglett.2c00404",

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AU - Cho, Yoon Sung

AU - Kim, Seung Tae

AU - Ryu, Do Hyun

PY - 2022/3/4

Y1 - 2022/3/4

N2 - A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts furan alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99%) with excellent enantioselectivity (up to >99% ee).

AB - A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts furan alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99%) with excellent enantioselectivity (up to >99% ee).

UR - https://www.scopus.com/pages/publications/85125683204

U2 - 10.1021/acs.orglett.2c00404

DO - 10.1021/acs.orglett.2c00404

M3 - Article

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AN - SCOPUS:85125683204

SN - 1523-7060

VL - 24

SP - 1732

EP - 1736

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Enantioselective Friedel-Crafts Alkylation of Furans with o-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst

Abstract

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