Construction of a New Class of Oxindole-Based Axially Chiral Styrenes via Kinetic Resolution

Application of 3-Alkyl-2-vinylindoles in Catalytic Asymmetric Dearomative (2+3) Cycloadditions

“…To address the above challenges and based on our long-lasting efforts on chiral indole chemistry, we designed a chiral phosphoric acid (CPA)-catalyzed asymmetric dearomative (2+3) cycloaddition of 3-alkyl-2-vinylindoles with azoalkenes for the construction of enantioenriched pyrroloindoline skeletons (Scheme ). In this reaction, azoalkenes attracted our attention because of their high reactivity acting as 1,3-dipole surrogates in the presence of CPA. , Recently, Lu’s group devised elegant approaches on CPA-catalyzed asymmetric (3+2) cycloadditions of azoalkenes with C3-substituted indoles or 3-vinylindoles (Scheme a).…”

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

“…Over the past decades, many efficient synthetic methodologies for functionalized carbazole derivatives have been successfully developed [12][13][14][15][16][17][18]. Because indoles are readily available materials, the direct extension of indoles to carbazole skeletons has a great advantage [19][20][21][22][23][24][25][26][27]. Therefore, the Diels-Alder reaction of activated 2-vinylindolines or 3-vinylindolines with diverse dienophiles has become the most attractive strategy for the synthesis of carbazole deriv- atives [28][29][30][31][32][33][34][35][36][37][38][39][40].…”

Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

“…To fulfill this task and in continuation of our ongoing efforts in the enantioselective synthesis of indole-based chiral heterocycles [32][33][34][35], we designed a chiral phosphoric acid [36][37][38][39][40][41][42][43][44] (CPA)-catalyzed asymmetric [2 + 4] cycloaddition of 3-vinylindoles with ortho-quinone methides (o-QMs) and their precursors (Figure 4). The o-QMs were selected To fulfill this task and in continuation of our ongoing efforts in the enantioselective synthesis of indole-based chiral heterocycles [32][33][34][35], we designed a chiral phosphoric acid [36][37][38][39][40][41][42][43][44] (CPA)-catalyzed asymmetric [2 + 4] cycloaddition of 3-vinylindoles with ortho-quinone methides (o-QMs) and their precursors (Figure 4). The o-QMs were selected as suitable reaction partners because of their high reactivity as oxa-dienes in catalytic asymmetric cycloadditions [45][46][47][48][49][50][51][52][53][54][55][56][57][58]…”

“…This dual activation mode of CPA facilitates regioselective and enantioselective [2 + 4] cycloaddition between 3-vinylindoles 1 and o-QMs 2, thus affording the chiral indole-containing chroman derivatives 3. To fulfill this task and in continuation of our ongoing efforts in the enantioselective synthesis of indole-based chiral heterocycles [32][33][34][35], we designed a chiral phosphoric acid [36][37][38][39][40][41][42][43][44] (CPA)-catalyzed asymmetric [2 + 4] cycloaddition of 3-vinylindoles with ortho-quinone methides (o-QMs) and their precursors (Figure 4). The o-QMs were selected as suitable reaction partners because of their high reactivity as oxa-dienes in catalytic asymmetric cycloadditions [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62][63].…”