Rhodium-Catalyzed Reaction of Silacyclobutanes with Unactivated Alkynes to Afford Silacyclohexenes

Hua Chen; Yi Chen; Xiaoxiao Tang; Shunfa Liu; Runping Wang; Tianbao Hu; Lu Gao; Zhenlei Song

doi:10.1002/anie.201814143

Rhodium-Catalyzed Reaction of Silacyclobutanes with Unactivated Alkynes to Afford Silacyclohexenes

Angew Chem Int Ed Engl. 2019 Mar 26;58(14):4695-4699. doi: 10.1002/anie.201814143. Epub 2019 Feb 27.

Authors

Hua Chen¹, Yi Chen¹, Xiaoxiao Tang¹, Shunfa Liu¹, Runping Wang¹, Tianbao Hu¹, Lu Gao¹, Zhenlei Song^{1

2}

Affiliations

¹ Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.
² State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China.

PMID: 30742358
DOI: 10.1002/anie.201814143

Abstract

A Rh-catalyzed reaction of silacyclobutanes (SCBs) with unactivated alkynes has been developed to form silacyclohexenes with high chemoselectivity. Good enantioselectivity at the stereogenic silicon center was achieved using a chiral phosphoramidite ligand. The resulting silacyclohexenes are useful scaffolds for synthesizing structurally attractive silacyclic compounds.

Keywords: alkynes; reaction mechanisms; rhodium; ring expansions; silacycles.

Abstract

Grants and funding