Tandem Reaction of Deprotonation-Oxidation-Wittig Reaction: Stereoselective Synthesis of (E)-α,β-Unsaturated Enoates

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Highly Stereoselective Synthesis of trans-3-Aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans

Multi-substituted dihydrofurans are valuable intermediates for the synthesis of natural products and pharmaceuticals. Considerable attention has been focused on the development of efficient and regioselective methods for their preparation. Using K2CO3 as a base, with the reaction of fur-2-oylmethyltriphenylarsonium bromide 1 and ethyl 2-acetyl-3-arylacrylate 2 in tetrahydrofuran at room temperature, we found an efficient protocol was achieved to synthesize trans-3-aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans 3 in good yield with high stereoselectivity. The structure of compound 3 was confirmed by IR, ^1H NMR, MS and HRMS. The mechanism for the formation of 3 was proposed.     

Synthesis of a New C-15 Phosphorus Ylide Used for the Preparation of Some β-End-Group Retinoid Derivatives

A synthesis of a new C-15 phosphorus ylide from a C-14 enaminone is reported. This reagent, which undergoes selective 1,2- or 1,4-additions with saturated and unsaturated aldehydes, may find some synthetic use for the preparation of β-end-group retinoid derivatives.     

XYZH systems as potential 1,3-dipoles. Part 62: 1,3-Dipolar cycloaddition reactions of metallo-azomethine ylides derived from α-iminophosphonates

Metallo-azomethine ylides, generated from iminophosphonates in combination with LiBr or AgOAc and bases Et₃N, DBU, t-butyl tetramethylguanidine(BTMG) undergo cycloaddition to give dialkyl pyrrolidine-2-phosphonates along with the corresponding Michael adduct in some cases. Cycloadditions with the chiral dipolarophile 5R-(1′R,2′S,5′R-menthyloxy)-2-(5H)-furanone (MOF) afforded enantiopure cycloadducts.     

区域和立体选择性合成新型螺羟吲哚类化合物

2-芳亚甲基苯并[4,5]咪唑并[2,1-b]噻唑-3-酮与甲亚胺叶立德(经靛红与肌氨酸反应在线生成)进行l,3-偶极环加成反应, 合成了8个新的螺羟吲哚类化合物. 采用元素分析, NMR, IR, 质谱以及X射线单晶衍射等多种谱学技术对产物进行详细表征, 而产物的晶体结构表明了此类反应具有高度的立体选择性和区域选择性.