Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-π-allyl catalyst

被引：11

作者：

Kitagawa, O ^{[1
]}

Takahashi, M ^{[1
]}

Kohriyama, M ^{[1
]}

Taguchi, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Hachioji, Tokyo 1920392, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo035305l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-,T-allyl catalyst to give atropisomeric N-allyl o-tert-butyl anilide derivatives.

引用

页码：9851 / 9853

页数：3

共 24 条

[1] Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst
Kitagawa, O
Kohriyama, M
Taguchi, T
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24): : 8682 - 8684
[2] Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral π-allyl Pd-catalyst
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Yotsumoto, K
Kohriyama, M
Dobashi, Y
Taguchi, T
ORGANIC LETTERS, 2004, 6 (20) : 3605 - 3607
[3] Catalytic asymmetric desymmetrization of meso-diamide derivatives through enantioselective N-allylation with a chiral π-allyl Pd catalyst:: Improvement and reversal of the enantioselectivity
Kitagawa, O
Matsuo, S
Yotsumoto, K
Taguchi, T
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06): : 2524 - 2527
[4] Synthesis of optically active atropisomeric anilide derivatives and their application to asymmetric reaction
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Taguchi, T
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2001, 59 (07) : 680 - 688
[5] Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides through Chiral Palladium-Catalyzed N-Allylation
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JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 8112 - 8120
[6] Catalytic Enantioselective Synthesis of N-C Axially Chiral N-(2,6-Disubstituted-phenyl)sulfonamides through Chiral Pd-Catalyzed N-Allylation
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MOLECULES, 2022, 27 (22):
[7] A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (14) : 2099 - 2102
[8] Optically active axially chiral anilide and maleimide derivatives as new chiral reagents: Synthesis and application to asymmetric Diels-Alder reaction
Kitagawa, O
Izawa, H
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Dobashi, A
Taguchi, T
Shiro, M
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08): : 2634 - 2640
[9] Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3676 - 3677
[10] Synthesis of oxazoles through Pd-catalyzed cycloisomerization-allylation of N-propargylamides with allyl carbonates
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Iimura, Koichi
Hanzawa, Yuji
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