Gold(I)-Catalyzed Tandem Intramolecular Methoxylation/Double Aldol Condensation Strategy Yielding 2,2'-Spirobi[indene] Derivatives

Jingfu Zhang; Sen Zhang; Zhixing Ding; Anbin Hou; Jiayue Fu; Hongwei Su; Maosheng Cheng; Bin Lin; Lu Yang; Yongxiang Liu

doi:10.1021/acs.orglett.2c02653

Gold(I)-Catalyzed Tandem Intramolecular Methoxylation/Double Aldol Condensation Strategy Yielding 2,2'-Spirobi[indene] Derivatives

Org Lett. 2022 Sep 23;24(37):6777-6782. doi: 10.1021/acs.orglett.2c02653. Epub 2022 Sep 14.

Authors

Jingfu Zhang^{1

2

3}, Sen Zhang^{1

2

3}, Zhixing Ding^{1

3}, Anbin Hou^{1

2

3}, Jiayue Fu^{1

2

3}, Hongwei Su^{1

2

3}, Maosheng Cheng^{1

3}, Bin Lin^{1

2

3}, Lu Yang^{1

2

3}, Yongxiang Liu^{1

2

3}

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang 110016, P.R. China.
² Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, P.R. China.
³ Institute of Drug Research in Medicine Capital of China, Benxi 117000, P.R. China.

PMID: 36103647
DOI: 10.1021/acs.orglett.2c02653

Abstract

The syntheses of 2,2'-spirobi[indene] derivatives based on a gold(I)-catalyzed tandem strategy involving intramolecular methoxylation/double aldol condensation were achieved. Examination of the scope of this tandem reaction by using a batch of alkynone substrates disclosed that the reaction possessed a good functional group tolerance. A cationic gold(I) catalyst/protonic acid-catalyzed mechanism for this tandem reaction is proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry
Catalysis
Gold* / chemistry
Indenes*

Substances

Aldehydes
Indenes
indene
Gold
3-hydroxybutanal