Chiral Spirocyclic Phosphoric Acids and Their Growing Applications

Abstract

What is the most favorite and original chemistry developed in your research group? Developing SPINOL-phosphoric acids (SPAs), TM-SPINOL-phosphoric acids (SPAs 2.0) and PCP-derived planar chiral phosphoric acids (PPAs) for asymmetric catalysis. What is the most important personality for scientific research? Curiosity, optimism, self-confidence and persistence. What's your hobbies? What's your favorite book(s)? I enjoy cooking. My favorite book is Journey to the West. Who influences you mostly in your life? My mother. What is your favorite journal(s)? The journals publishing the original and systematic work of synthetic chemistry. Could you please give us some advices on improving Chinese Journal of Chemistry? Fast review, fast publication, fast promotion via new media.

Enantioselective synthesis of indole‐based unnaturalβ‐Alkynylα‐amino acid derivatives via chiral phosphoric acid catalysis

“…To test the feasibility of our design, we began our studies with the enantioselective C-3 functionalization of indole substrate 1a with the β,γ-alkynyl-α-imino ester 2a (see the supporting information) in the presence of 10 mol% chiral spirocyclic phosphoric acid (S)-A1 developed by our group [41][42][43][44][45][46][47][48] in dichloromethane at room temperature. Fortunately, the transformation proceeded smoothly and the corresponding product, a chiral indole-β-alkynylα-amino acid derivative, was obtained in 61% yield with 35% ee within 4 h (Table 1, entry 1).…”

“…37 Moreover, in 2010, the Bolm group reported an enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a -CF 3 unit via chiral Brønsted acid catalysis. 38 Here, we envisioned to develop an organocatalytic asymmetric synthesis of indole-based unnatural β-alkynyl-α-amino acid derivatives with the chiral phosphoric acid [39][40][41][42][43][44][45][46][47][48] as a catalyst (Scheme 1D), and the strategy is atom-economical and the reaction proceeds without any additives. The significant challenge is to select suitable chiral catalysts to control regioselectivity and stereoselectivity during this asymmetric transformation.…”

Recent Progress in Metal‐Organic Frameworks@Cellulose Hybrids and Their Applications

“…[ 1‐4 ] Compared with zeolites, active carbons, and mesoporous silicas, MOFs possess particular features, such as tunable structures, facile functionalization and incorporation of active sites. [ 5‐9 ] Thanks to these unique advantages, the application fields of MOFs cover gas storage/separation, [ 10‐13 ] catalysis, [ 14‐17 ] sensing, [ 18‐22 ] environmental remediation, [ 23‐27 ] proton conduction, [ 28‐31 ] energy storage, [ 32‐34 ] and even biomedical applications. [ 35‐38 ] Nevertheless, the large‐ scale commercialization of MOFs is seriously limited because of their intrinsic fragility, mechanical instability, and unworkability.…”

A breakthrough in 2-indolylmethanol-involved organocatalytic asymmetric reactions

“…Among different approaches, 2-indolylmethanols have been recognized as a class of versatile platform molecules in organocatalytic asymmetric transformations for constructing chiral indole-based scaffolds [1][2][3] . As summarized in Figure 1A, under the catalysis of chiral Brønsted acid (B*-H) [4][5] , 2-indolylmethanols readily undergo dehydration to generate carbocation intermediates A-B and vinyliminiums C, which can be illustrated as delocalized cations D. Due to the steric effect of the two R groups (particularly when R is an aryl group), nucleophiles (Nu) more readily attack carbocation B than carbocation A, thus resulting in the C3-umpolung reactivity of 2-indolylmethanols [1][2] . Namely, the C3position of the indole ring is changed from nucleophilic to electrophilic.…”