Synthesis of Optically Active Atropisomeric Anilide Derivatives through Diastereoselective N-Allylation with a Chiral Pd-π-Allyl Catalyst

Osamu Kitagawa; Masashi Takahashi; Mitsuteru Kohriyama; Takeo Taguchi

doi:10.1021/jo035305l

Synthesis of Optically Active Atropisomeric Anilide Derivatives through Diastereoselective N-Allylation with a Chiral Pd-π-Allyl Catalyst

Osamu Kitagawa, Masashi Takahashi, Mitsuteru Kohriyama, Takeo Taguchi

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

9 Citations (Scopus)

Abstract

N-Allylation of o-tert-butyl anilides derived from o-tert-butyl aniline and (S)-lactic acid or (S)-mandelic acid proceeded with high diastereoselectivity in the presence of a (BINAP)Pd-π-allyl catalyst to give atropisomeric N-allyl o-tert-butyl anilide derivatives.

Original language	English
Pages (from-to)	9851-9853
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	68
Issue number	25
DOIs	https://doi.org/10.1021/jo035305l
Publication status	Published - 2003 Dec 12
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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abstract = "N-Allylation of o-tert-butyl anilides derived from o-tert-butyl aniline and (S)-lactic acid or (S)-mandelic acid proceeded with high diastereoselectivity in the presence of a (BINAP)Pd-π-allyl catalyst to give atropisomeric N-allyl o-tert-butyl anilide derivatives.",

author = "Osamu Kitagawa and Masashi Takahashi and Mitsuteru Kohriyama and Takeo Taguchi",

year = "2003",

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AU - Takahashi, Masashi

AU - Kohriyama, Mitsuteru

AU - Taguchi, Takeo

PY - 2003/12/12

Y1 - 2003/12/12

N2 - N-Allylation of o-tert-butyl anilides derived from o-tert-butyl aniline and (S)-lactic acid or (S)-mandelic acid proceeded with high diastereoselectivity in the presence of a (BINAP)Pd-π-allyl catalyst to give atropisomeric N-allyl o-tert-butyl anilide derivatives.

AB - N-Allylation of o-tert-butyl anilides derived from o-tert-butyl aniline and (S)-lactic acid or (S)-mandelic acid proceeded with high diastereoselectivity in the presence of a (BINAP)Pd-π-allyl catalyst to give atropisomeric N-allyl o-tert-butyl anilide derivatives.

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Synthesis of Optically Active Atropisomeric Anilide Derivatives through Diastereoselective N-Allylation with a Chiral Pd-π-Allyl Catalyst

Abstract

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