Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst

Osamu Kitagawa; Mitsuteru Kohriyama; Takeo Taguchi

doi:10.1021/jo0264271

Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst

Osamu Kitagawa, Mitsuteru Kohriyama, Takeo Taguchi

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

94 Citations (Scopus)

Abstract

Catalytic asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate proceeds in the presence of tol-BINAP-Pd catalyst to give chiral N-allyl ortho-tert-butylanilides of 32-44%ee in excellent chemical yields (≥ 90%).

Original language	English
Pages (from-to)	8682-8684
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	67
Issue number	24
DOIs	https://doi.org/10.1021/jo0264271
Publication status	Published - 2002 Nov 29
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo0264271

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title = "Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst",

abstract = "Catalytic asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate proceeds in the presence of tol-BINAP-Pd catalyst to give chiral N-allyl ortho-tert-butylanilides of 32-44%ee in excellent chemical yields (≥ 90%).",

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

year = "2002",

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doi = "10.1021/jo0264271",

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AU - Kitagawa, Osamu

AU - Kohriyama, Mitsuteru

AU - Taguchi, Takeo

PY - 2002/11/29

Y1 - 2002/11/29

N2 - Catalytic asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate proceeds in the presence of tol-BINAP-Pd catalyst to give chiral N-allyl ortho-tert-butylanilides of 32-44%ee in excellent chemical yields (≥ 90%).

AB - Catalytic asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate proceeds in the presence of tol-BINAP-Pd catalyst to give chiral N-allyl ortho-tert-butylanilides of 32-44%ee in excellent chemical yields (≥ 90%).

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DO - 10.1021/jo0264271

M3 - Article

C2 - 12444660

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst

Abstract

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