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

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

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

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).

Original language	English
Pages (from-to)	4436-4439
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.5b02089
Publication status	Published - Sept 18 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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).",

author = "Hiroki Mandai and Takuma Fujiwara and Katsuaki Noda and Kazuki Fujii and Koichi Mitsudo and Toshinobu Korenaga and Seiji Suga",

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year = "2015",

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T1 - Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives

AU - Mandai, Hiroki

AU - Fujiwara, Takuma

AU - Noda, Katsuaki

AU - Fujii, Kazuki

AU - Mitsudo, Koichi

AU - Korenaga, Toshinobu

AU - Suga, Seiji

PY - 2015/9/18

Y1 - 2015/9/18

N2 - 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).

AB - 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).

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JO - Organic Letters

JF - Organic Letters

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ER -

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

Abstract

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