19158-57-7Relevant academic research and scientific papers
Water-Mediated Intramolecular Cyclization/Oxidation of α-Carbonyl Sulfur Ylides: Synthesis of Corey-Chaykovsky Reagent Type Heterocycles
Kang, Xiaokang,Liang, Xiayu,Zeng, Qingle
supporting information, p. 7477 - 7481 (2021/10/12)
A new class of Corey-Chaykovsky reagent type five-membered heterocycles with an oxosulfonium ylide moiety has been synthesized by the water-mediated intramolecular cyclization/oxidation of α-carbonyl sulfur ylides generated in situ from sulfonium salts under mild conditions.
Catalyst-Free Synthesis of 2,3-Dihydrobenzofurans via a Formal [4+1] Annulation of Propargylamines with Sulfur Ylides
He, Xinwei,Xie, Mengqing,Tang, Qiang,Zuo, Youpeng,Li, Ruxue,Shang, Yongjia
, p. 11623 - 11638 (2019/10/02)
A simple, general route to the 2,3-dihydrobenzofurans substituted at C3 by an aryethynyl or aryl group, starting from propargylamine and its derivatives with benzoyl sulfonium salts, has been developed. This reaction involved an in situ generated o-quinone methide (o-QM) intermediate followed by [4+1] annulation with sulfur ylides. Notably, this protocol's features include moderate to excellent yields and remarkable diastereoselectivity (>20:1 dr in general), easy performance, as well as applicability to versatile 2,3-dihydrobenzofurans with aryethynyl or an aryl group via C-C and C-O bond formation in one pot without any catalyst in an aqueous mixed solvent.
Synthesis of functionalized thietanes via electrophilic carbenoid-induced ring expansion of thiiranes with sulfonium acylmethylides as carbene precursors
Dong, Jun,Du, Hongguang,Xu, Jiaxi
, p. 10724 - 10739 (2019/09/30)
Various functionalized thietanes were prepared from thiiranes via an electrophilic ring expansion with rhodium carbenoids as electrophiles generated from safe and readily accessible dimethylsulfonium acylmethylides. The reaction appears to proceed through electrophilic metallocarbenoid-induced activation of thiiranes, nucleophilic ring-opening of the activated thiiranes with dimethyl sulfide as a transient nucleophile, and nucleophilically intramolecular cyclization. The Umpolung from the nucleophilic ylides to the electrophilic carbenoids plays an important role in both the activation and ring opening of thiiranes and subsequent cyclization. The current method provides a new strategy for the efficient preparation of functionalized thietanes from readily available thiiranes.
1,6-Conjugated Addition-Mediated [2+1] Annulation: Approach to Spiro[2.5]octa-4,7-dien-6-one
Yuan, Zhenbo,Fang, Xinxin,Li, Xuanyi,Wu, Jie,Yao, Hequan,Lin, Aijun
, p. 11123 - 11130 (2015/11/18)
A formal 1,6-conjugated addition-mediated [2+1] annulation to synthesize spiro[2.5]octa-4,7-dien-6-one with p-quinone methides and sulfur ylides has been described. This domino-type process was highly diastereoselective and exhibited good functional group tolerance and scalability without the use of metals and bases.
