Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives

Hiroki Mandai; Takuma Fujiwara; Katsuaki Noda; Kazuki Fujii; Koichi Mitsudo; Toshinobu Korenaga; Seiji Suga

doi:10.1021/acs.orglett.5b02089

Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives

Org Lett. 2015 Sep 18;17(18):4436-9. doi: 10.1021/acs.orglett.5b02089. Epub 2015 Sep 10.

Authors

Hiroki Mandai¹, Takuma Fujiwara¹, Katsuaki Noda¹, Kazuki Fujii¹, Koichi Mitsudo¹, Toshinobu Korenaga², Seiji Suga^{1

3

4}

Affiliations

¹ Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
² Faculty of Engineering, Department of Chemistry and Bioengineering, Iwate University, Morioka , Iwate 020-8551, Japan.
³ Research Center of New Functional Materials for Energy Production, Storage and Transport, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
⁴ Japan Science and Technology Agency, ACT-C , 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

PMID: 26356582
DOI: 10.1021/acs.orglett.5b02089

Abstract

Chiral N,N-4-(dimethylamino)pyridine (DMAP) derivatives, which can be readily prepared by the Ugi multicomponent reaction in a one-pot manner, have been efficiently applied to the enantioselective Steglich rearrangement of oxindole derivatives to give the desired products bearing a quaternary carbon center in high yield (>98% yield) and with high enantioselectivity (up to 99:1 er).