Asymmetric Chlorination/ring Expansion for the Synthesis of α-quaternary Cycloalkanones

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2014 Mar 13

PMID 24617607

Citations 10

Authors

Qin Yin

Shu-Li You

Affiliations

Soon will be listed here.

Abstract

A highly enantioselective chlorination/ring expansion cascade for the construction of cycloalkanones with an all-carbon quaternary center was realized (up to 97% ee). Oxa-cyclobutanol substrates were employed for the first time in the ring expansion reactions, affording the functionalized dihydrofuranones in excellent enantioselectivity.

Citing Articles

Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols.

Cao R, Su R, Wei Z, Li Z, Zhu D, Huo Y Nat Commun. 2025; 16(1):2147.

PMID: 40032867 PMC: 11876436. DOI: 10.1038/s41467-025-57381-w.

A Domino Radical Amidation/Semipinacol Approach to All-Carbon Quaternary Centers Bearing an Aminomethyl Group.

Dhak M, Arunprasath D, Argent S, Cuthbertson J Chemistry. 2023; 29(47):e202300922.

PMID: 37278542 PMC: 10947466. DOI: 10.1002/chem.202300922.

Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols.

Capel E, Rodriguez-Rodriguez M, Uria U, Pedron M, Tejero T, Vicario J J Org Chem. 2021; 87(1):693-707.

PMID: 34928602 PMC: 8749959. DOI: 10.1021/acs.joc.1c02699.

3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.

Lai Z, Zhang R, Feng Q, Sun J Chem Sci. 2021; 11(36):9945-9949.

PMID: 34094256 PMC: 8162131. DOI: 10.1039/d0sc04254d.

Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes.

Sandvoss A, Wiest J Chemistry. 2020; 27(19):5871-5879.

PMID: 33274788 PMC: 8049043. DOI: 10.1002/chem.202004923.