Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions

Construction of Optically Active Indolines by Formal [4+1] Annulation of Sulfur Ylides and N‐(ortho‐Chloromethyl)aryl Amides

“…Indolines constitute the core structure of numerous pharmaceuticals and alkaloid natural products, displaying a range of diverse biological activities 1. In particular, chiral 2‐substituted indolines are of great significance with extensive applications as therapeutic reagents,2a,b as well as chiral auxiliaries 2c. Representative examples include oleraceins A–D,3a isolated from the edible plant Portulaca oleracea utilized in Chinese traditional medicine, the antihypertensive drug pentopril 3b (angiotensin‐converting enzyme inhibitor), and benzastatins E–G3c from the culture broth of Streptomyces nitrosporeus 30643 as neuronal cell‐protecting substances (Figure 1).…”

Anionic–Anionic Asymmetric Tandem Reactions: One‐Pot Synthesis of Optically Pure Fluorinated Indolines from 2‐p‐Tolylsulfinyl Alkylbenzenes

“…Indolines have also been successfully employed as chiral auxiliaries in asymmetric synthesis. [4] Consequently, a number of multistep strategies have been developed for synthesizing these compounds. [5] However, no short and efficient methods for the preparation of enantiomerically pure substituted indolines have been developed to date, therefore the search for new methods for synthesizing them remains a challenge.…”

Asymmetric tandem reactions: New synthetic strategies

“…Additionally, this framework has also been successfully employed as chiral auxiliary in asymmetric synthesis [14]. Accordingly, this structural motif has stimulated the development of a wide range of methods aimed at the stereoselective construction or functionalization of indoline rings [15].…”