Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

6-2015

Journal or Book Title

Organic Letters

Volume

17

Issue

13

First Page

3276

Last Page

3279

DOI

10.1021/acs.orglett.5b01447

Abstract

Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted chroman-4-ones in high yields with excellent diastereoselectivity.

Comments

Reprinted (adapted) with permission from Organic Letters 17 (2015): 3276, doi:10.1021/acs.orglett.5b01447. Copyright © 2015 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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