Gold-Catalyzed Regio- and Diastereoselective [3 + 2] Cycloaddition/Unactivated C(sp3)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles

Rui Hu; Xiaowen Ji; Yongsheng Zhang; Philip Wai Hong Chan; Weidong Rao

doi:10.1021/acs.orglett.5c00891

Gold-Catalyzed Regio- and Diastereoselective [3 + 2] Cycloaddition/Unactivated C(sp³)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles

Rui Hu, Xiaowen Ji, Yongsheng Zhang, Philip Wai Hong Chan, Weidong Rao

School of Chemistry

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

1 Citation (Scopus)

Abstract

An efficient and expeditious method to assemble oxa-bridged polycycles bearing up to six contiguous stereocenters from a gold(I)-catalyzed [3 + 2] cycloaddition/unactivated C(sp³)-H bond insertion cascade of o-1,6-enynyl benzaldehydes at a low catalyst loading of 2 mol % is described.

Original language	English
Pages (from-to)	3958–3963
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.5c00891
Publication status	Published - 4 Apr 2025

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10.1021/acs.orglett.5c00891

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title = "Gold-Catalyzed Regio- and Diastereoselective [3 + 2] Cycloaddition/Unactivated C(sp3)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles",

abstract = "An efficient and expeditious method to assemble oxa-bridged polycycles bearing up to six contiguous stereocenters from a gold(I)-catalyzed [3 + 2] cycloaddition/unactivated C(sp3)-H bond insertion cascade of o-1,6-enynyl benzaldehydes at a low catalyst loading of 2 mol \% is described.",

author = "Rui Hu and Xiaowen Ji and Yongsheng Zhang and Chan, \{Philip Wai Hong\} and Weidong Rao",

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AU - Hu, Rui

AU - Ji, Xiaowen

AU - Zhang, Yongsheng

AU - Chan, Philip Wai Hong

AU - Rao, Weidong

PY - 2025/4/4

Y1 - 2025/4/4

N2 - An efficient and expeditious method to assemble oxa-bridged polycycles bearing up to six contiguous stereocenters from a gold(I)-catalyzed [3 + 2] cycloaddition/unactivated C(sp3)-H bond insertion cascade of o-1,6-enynyl benzaldehydes at a low catalyst loading of 2 mol % is described.

AB - An efficient and expeditious method to assemble oxa-bridged polycycles bearing up to six contiguous stereocenters from a gold(I)-catalyzed [3 + 2] cycloaddition/unactivated C(sp3)-H bond insertion cascade of o-1,6-enynyl benzaldehydes at a low catalyst loading of 2 mol % is described.

UR - https://www.scopus.com/pages/publications/105002036718

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DO - 10.1021/acs.orglett.5c00891

M3 - Article

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SN - 1523-7060

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SP - 3958

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JO - Organic Letters

JF - Organic Letters

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ER -

Gold-Catalyzed Regio- and Diastereoselective [3 + 2] Cycloaddition/Unactivated C(sp³)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles

Abstract

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New ion-pair species-driven strategies for complex molecule synthesis

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Gold-Catalyzed Regio- and Diastereoselective [3 + 2] Cycloaddition/Unactivated C(sp3)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles

Abstract

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New ion-pair species-driven strategies for complex molecule synthesis

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Gold-Catalyzed Regio- and Diastereoselective [3 + 2] Cycloaddition/Unactivated C(sp³)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles