文献类型：期刊文献

英文题名：Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,3-Diketones with Keto-Vinylidenecyclopropanes: Synthesis of Enantiomerically Enriched Cyclic β-Amino Alcohols

作者：Xu, Chen[1,2];Ning, Chao[1,2];Yang, Song[1,2];Wei, Yin[3];Shi, Min[1,2,3]

机构：[1]East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, State Key Lab Organometall Chem, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem, 354 Fenglin Lu, Shanghai 200032, Peoples R China

年份：2021

卷号：363

期号：6

起止页码：1727

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000616387300001)，CCR-EXPANDED(收录号:WOS:000616387300001)】；

基金：We are grateful for the financial support from the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000) and sioczz201808, the National Natural Science Foundation of China (21372250, 21121062, 21302203, 20732008, 21772037, 21772226, 21861132014 and 91956115).

语种：英文

外文关键词：β -amino alcohols; trimethylenemethane-rhodium (TMM-Rh) complex; vinylidenecyclopropanes (VDCPs); diketone; C− H alkylation

摘要：We report here an effective and atom-economical method to synthesize enantiomerically enriched cyclic beta-amino alcohols via a rhodium-catalyzed asymmetric cycloisomerization of 1,3-diketones with keto-vinylidenecyclopropanes. The reactions proceed through a Rh-catalyzed transformation of keto-vinylidenecyclopropanes via cleavage of the distal C-C bond of the three-membered ring as a three-carbon synthon, allowing the generation of a range of enantiomerically enriched cyclic beta-amino alcohols tethered to an alkene and an 1,3-dione moiety in good yields with high ee values under mild conditions. Derivatizations including allylation of the functionalized beta-amino alcohols and subsequent RCM reaction as well as the preparation of a pyrazole derivative were carried out as well.