Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition

1Citations
Citations of this article
6Readers
Mendeley users who have this article in their library.

Abstract

An efficient method was developed for the synthesis of dihydro-2H-spiro[benzofuran-3,2'-[1,3]dithiane]-2,5(4H)-diones I [R = Me, (CH2)2CO2Me, Ph, etc., R1 = H, Me] and tert-butyl-2,5-dioxohexahydro-2H-spiro[furo[2,3-d]indole-3,2'-[1,3]dithiane]-7(3aH)-carboxylate via phosphazene-catalyzed desymmetrizing intramol. conjugate addn. of a tethered dithiane nucleophile to cyclohexadienones under mild reaction conditions. The products I participated in diastereoselective convex-facial addns., leading to 5-hydroxy-7a-dimethyl-3a,4,5,7a-tetrahydro-2H-spiro[benzofuran-3,2'-[1,3]dithian]-2-ones II [R2 = H, Me]. [on SciFinder(R)]

Cite

CITATION STYLE

APA

Horwitz, M. A., Massolo, E., & Johnson, J. S. (2017). Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition. Beilstein Journal of Organic Chemistry, 13, 762–767. https://doi.org/10.3762/bjoc.13.75

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free