Highly Diastereoselective Multicomponent Cascade Reactions: Efficient Synthesis of Functionalized 1‐Indanols

Triflic Acid-Catalyzed Synthesis of Indole-Substituted Indane Derivatives via In Situ Formed Acetal-Facilitated Nucleophilic Addition and 4π-Electron-5-Carbon Electrocyclization Sequence

“…Notably, Crixivan, developed by Merck, is an HIV protease inhibitor used as an important drug for the treatment of AIDS, and resveratrol-derived natural products such as caraphenols, α-diisoeugenol, and endothelin receptor antagonist SB 209670 are a few other biologically important compounds to mention (Figure ). Owing to their widespread natural and biological relevance, the indane scaffold attracted researchers to pursue its chemical synthesis, and different protocols have been reported in literature for the synthesis of indane derivatives in both racemic and asymmetric manners. − …”

Asymmetric Synthesis of 1,3-Oxazolidine Derivatives with Multi-Component Reaction and Research of Kinetic Resolution

“…As a result, more and more efficient syntheses of 1,3-oxazolidine derivatives were reported utilizing intramolecular cyclization and intermolecular cycloaddition [14,15]. Cascade reaction, an ecologically- and economically-favorable method, was considered to fall under the banner of “green chemistry” because of its atom and resource economy [16,17,18,19], as well as time efficiency [20,21,22,23,24,25,26,27,28,29]. However, cascade reaction has not been used to construct 1,3-oxazolidine skeleton up to date.…”

Recent Advances in the Synthesis of Indanes and Indenes

“…Cascade processes initiated by a Michael‐type intermolecular reaction and followed by carbocyclization are also powerful methods for the synthesis of indanes. Thus, the Rh‐catalyzed highly diastereoselective multicomponent cascade reaction between diazo compounds 52 , an alcohol and ( E )‐2‐(3‐oxo‐3‐arylprop‐1‐enyl)benzaldehydes 53 led to functionalized indan‐1‐ols 54 (Scheme ), while the Rh‐catalyzed reaction between boronic acids with electron‐deficient o ‐divinylbenzenes 55 afforded all‐ trans 1,2,3‐trisubstituted indanes 56 with good diastereoselectivities (Scheme ) . The enantioselective synthesis of nonracemic 3‐aryl‐1‐indanones by a rhodium‐catalyzed intramolecular 1,4‐addition of pinacolborane chalcone derivatives, using Mono‐Phos as nonracemic ligand, has also been reported …”

“… Diastereoselective synthesis of indan‐1‐ol derivatives 54 by the Rh‐catalyzed cascade reaction between diazo compounds 52 , an alcohol and ( E )‐2‐(3‐oxo‐3‐arylprop‐1‐enyl)benzaldehydes 53 …”