Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2021 Oct 7

PMID 34615353

Citations 4

Authors

Carlos Diez-Poza

Asuncion Barbero

Affiliations

Soon will be listed here.

Abstract

The silyl-Prins cyclization of geminal vinylsilyl alcohols and aldehydes, promoted by TMSOTf, provides access to polysubstituted tetrahydropyrans in which the silyl group remains in the molecule and an aryl group has migrated from silicon to carbon. This domino silyl-Prins/aryl migration process is general and high-yielding for aryl, vinyl, or alkyl aldehydes. Moreover, cyclization proceeds with very high stereocontrol in a one-pot reaction in which both quaternary and tertiary stereogenic centers have been created.

Citing Articles

Terminal Cyclopropylsilyl Alcohols as Useful Key Units to Access 2,3,4,6-Tetrasubstituted Tetrahydropyran Scaffolds by Stereocontrolled Prins Cyclization.

Pena L, Barbero A Org Lett. 2024; 26(24):5202-5207.

PMID: 38856097 PMC: 11197095. DOI: 10.1021/acs.orglett.4c01806.

Towards an efficient methodology for the synthesis of functionalized dihydropyrans by silyl-Prins cyclization: access to truncated natural products.

Pena L, Gonzalez-Andres P, Barbero A RSC Adv. 2024; 14(1):707-711.

PMID: 38173586 PMC: 10762716. DOI: 10.1039/d3ra07520f.

Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound.

Diez-Poza C, Fernandez-Pena L, Gonzalez-Andres P, Barbero A J Org Chem. 2023; 88(11):6776-6783.

PMID: 37220201 PMC: 10242753. DOI: 10.1021/acs.joc.3c00050.

Diastereoselective Synthesis of -2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways.

Pena L, Lopez E, Sanchez-Gonzalez A, Barbero A Molecules. 2023; 28(7).

PMID: 37049842 PMC: 10096261. DOI: 10.3390/molecules28073080.

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