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Divergent synthesis of polysubstituted cyclopropanes and beta-silyoxy imidates via switchable additions of N-tert-butanesulfinylimidates to acylsilanes
Tang, F (Tang, Fan)[ 1,2 ]; Ma, PJ (Ma, Peng-Ju)[ 1,2 ]; Yao, Y (Yao, Yun)[ 3 ]; Xu, YJ (Xu, Yan-Jun)[ 1 ]; Lu, CD (Lu, Chong-Dao)[ 1,3 ]
2019
Source PublicationCHEMICAL COMMUNICATIONS
ISSN1359-7345
Volume55Issue:26Pages:3777-3780
Abstract

Products derived from the reaction between N-tert-butanesulfinyl imidates and acylsilanes can be tuned by choosing appropriate bases and solvents. Here we show that in the presence of NaHMDS/THF, addition of enolized N-tert-butanesulfinyl imidates to acylsilanes and subsequent [1,2]-Brook rearrangement generate beta-silyloxy anion intermediates that undergo intramolecular cyclization to afford polysubstituted cyclopropanes. In the presence of (BuOK)-Bu-t/toluene, the reaction generates beta-silyloxy imidates as the protonation products of the beta-silyloxy anion intermediates. Both reactions are highly diastereoselective.

DOI10.1039/c9cc00963a
Indexed BySCI
WOS IDWOS:000464325900018
Citation statistics
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5725
Collection省部共建新疆特有药用资源利用重点实验室
Affiliation1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Yunnan Univ, Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Tang, F ,Ma, PJ ,Yao, Y ,et al. Divergent synthesis of polysubstituted cyclopropanes and beta-silyoxy imidates via switchable additions of N-tert-butanesulfinylimidates to acylsilanes[J]. CHEMICAL COMMUNICATIONS,2019,55(26):3777-3780.
APA Tang, F ,Ma, PJ ,Yao, Y ,Xu, YJ ,&Lu, CD .(2019).Divergent synthesis of polysubstituted cyclopropanes and beta-silyoxy imidates via switchable additions of N-tert-butanesulfinylimidates to acylsilanes.CHEMICAL COMMUNICATIONS,55(26),3777-3780.
MLA Tang, F ,et al."Divergent synthesis of polysubstituted cyclopropanes and beta-silyoxy imidates via switchable additions of N-tert-butanesulfinylimidates to acylsilanes".CHEMICAL COMMUNICATIONS 55.26(2019):3777-3780.
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