Synthesis of benzoxazoles via an amine-catalyzed [4 + 1] annulation

Aiguo Song; Xiaobei Chen; Xixi Song; Xinshuai Zhang; Shilei Zhang; Wei Wang

doi:10.1021/ol400988e

Synthesis of benzoxazoles via an amine-catalyzed [4 + 1] annulation

Aiguo Song, Xiaobei Chen, Xixi Song, Xinshuai Zhang, Shilei Zhang, Wei Wang

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

16 Scopus citations

Abstract

An unprecedented simple pyrrolidine catalyzed [4 + 1] annulation reaction of ynals with N-protected-2-aminophenols is reported. The utilization of the unique property and reactivity of the C=C triple bond in ynals leads to two consecutive conjugate addition reactions at the same β-position with pyrrolidine via iminium activation. The powerful cascade process affords a new alternative approach to biologically and synthetically important benzoxazoles in high yields (83-95%).

Original language	English (US)
Pages (from-to)	2510-2513
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	10
DOIs	https://doi.org/10.1021/ol400988e
State	Published - May 17 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An unprecedented simple pyrrolidine catalyzed [4 + 1] annulation reaction of ynals with N-protected-2-aminophenols is reported. The utilization of the unique property and reactivity of the C=C triple bond in ynals leads to two consecutive conjugate addition reactions at the same β-position with pyrrolidine via iminium activation. The powerful cascade process affords a new alternative approach to biologically and synthetically important benzoxazoles in high yields (83-95%).",

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T1 - Synthesis of benzoxazoles via an amine-catalyzed [4 + 1] annulation

AU - Song, Aiguo

AU - Chen, Xiaobei

AU - Song, Xixi

AU - Zhang, Xinshuai

AU - Zhang, Shilei

AU - Wang, Wei

PY - 2013/5/17

Y1 - 2013/5/17

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AB - An unprecedented simple pyrrolidine catalyzed [4 + 1] annulation reaction of ynals with N-protected-2-aminophenols is reported. The utilization of the unique property and reactivity of the C=C triple bond in ynals leads to two consecutive conjugate addition reactions at the same β-position with pyrrolidine via iminium activation. The powerful cascade process affords a new alternative approach to biologically and synthetically important benzoxazoles in high yields (83-95%).

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JF - Organic Letters

SN - 1523-7060

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Synthesis of benzoxazoles via an amine-catalyzed [4 + 1] annulation

Abstract

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