Literature DB >> 26356582

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

Hiroki Mandai1, Takuma Fujiwara1, Katsuaki Noda1, Kazuki Fujii1, Koichi Mitsudo1, Toshinobu Korenaga2, Seiji Suga1,3,4.   

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).

Entities:  

Year:  2015        PMID: 26356582     DOI: 10.1021/acs.orglett.5b02089

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

Review 1.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

2.  Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.

Authors:  Masaki Hayashi; Shoshana Bachman; Satoshi Hashimoto; Chad C Eichman; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-07-15       Impact factor: 15.419

3.  Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit.

Authors:  Chien-Tien Chen; Cheng-Che Tsai; Pei-Kang Tsou; Gou-Tao Huang; Chin-Hui Yu
Journal:  Chem Sci       Date:  2016-08-25       Impact factor: 9.825

4.  Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions.

Authors:  Hiroki Mandai; Kazuki Fujii; Hiroshi Yasuhara; Kenko Abe; Koichi Mitsudo; Toshinobu Korenaga; Seiji Suga
Journal:  Nat Commun       Date:  2016-04-15       Impact factor: 14.919

  4 in total

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