A Facile and Efficient Synthesis of Functionalized γ-Butyrolactones from Baylis - Hillman Adducts of Isatin

Abstract

A facile and efficient stereoselective synthesis of functionalized substituted γ-butyrolactones in excellent yield from the Baylis-Hillman adducts of isatin derivatives by a reductive cyclization methodology is reported.

Tunable Bifunctional Phosphine–Squaramide Promoted Morita–Baylis–Hillman Reaction of N‐Alkyl Isatins with Acrylates

“…(R)-Methyl 2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)acrylate (10 a): [11] (R)-Methyl 2-(3-hydroxy-5-methoxy-1-methyl-2-oxoindolin-3-yl)acrylate (10 g):y ellow oil, (21.7 Synthesis of g-butyrolactone 11 [26] To as olution of MBH adduct 10 c (0.2 mmol) in 4mLc osolvent of THF/water (9:1 v/v) was added NaBH 4 in an icewater bath. After the consumption of MBH adduct 10 c, which was monitoredbyT LC,t he reactionwas quenched by as aturated NH 4 Cl solution.T he aqueous phase was extracted by CH 2 Cl 2 (5 mL 3 ), then the combined organic phase was dried with anhydrous Na 2 SO 4, followed by filtration.…”

Highly Enantioselective Organocatalytic Asymmetric Mukaiyama-aldol Reaction of Difluoroenoxysilanes withβ,γ-Unsaturatedα-Ketoesters

“…该反应得到的手性叔醇化合物 3 具有碳碳双键、酮羰基和酯基, 可方便进行各种转化. 例如, 在 NaBH 4 作为还原剂的情况下 [15] , 产物 3g 中的 酮羰基和酯基均被还原成醇, 从而以 48%的产率, 90% 的 ee 值及 10∶1 非对映选择性得到多羟基化合物 14. 而 采用三乙基硅氢作为还原剂时 [16] , 则选择性地还原酮羰 基, 以 71%的产率, 90%的 ee 值及 …”

Synthesis of functionalized 1,2,3‐triazole derivatives of 2‐indolones from Morita‐Baylis‐Hillman adducts of isatin via “click chemistry”

“…play an important role as synthons for a number of potential synthetic intermediates and natural product syntheses [10]. As part of our on going research on novel synthetic applications of MBH adducts [11][12][13], particularly for the construction of novel oxindole derivatives [14][15][16][17][18], we were interested to explore the synthesis of title compounds using the versatile ''click chemistry'' reaction methodology. Several methods have been reported for the synthesis of 1,2,3-triazoles and 1,3-dipolar cycloaddition of azides to alkynes [19][20][21].…”