Direct asymmetric mannich-type reaction of α-isocyanoacetates with ketimines using cinchona alkaloid/copper(II) catalysts

Masashi Hayashi; Masaru Iwanaga; Noriyuki Shiomi; Daisuke Nakane; Hideki Masuda; Shuichi Nakamura

doi:10.1002/anie.201404629

Direct asymmetric mannich-type reaction of α-isocyanoacetates with ketimines using cinchona alkaloid/copper(II) catalysts

Masashi Hayashi, Masaru Iwanaga, Noriyuki Shiomi, Daisuke Nakane, Hideki Masuda, Shuichi Nakamura

化学科

研究成果: Article › 査読

106 被引用数 (Scopus)

抄録

The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)₂ and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.

本文言語	English
ページ（範囲）	8411-8415
ページ数	5
ジャーナル	Angewandte Chemie - International Edition
巻	53
号	32
DOI	https://doi.org/10.1002/anie.201404629
出版ステータス	Published - 4 8月 2014

文献へのアクセス

10.1002/anie.201404629

他のファイルとリンク

Scopusの出版物のリンク

引用スタイル

@article{97fc1ef7d0c54d8da2004008710f7614,

title = "Direct asymmetric mannich-type reaction of α-isocyanoacetates with ketimines using cinchona alkaloid/copper(II) catalysts",

abstract = "The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.",

keywords = "Lewis acid, alkaloids, asymmetric synthesis, copper, organocatalysis",

author = "Masashi Hayashi and Masaru Iwanaga and Noriyuki Shiomi and Daisuke Nakane and Hideki Masuda and Shuichi Nakamura",

year = "2014",

month = aug,

day = "4",

doi = "10.1002/anie.201404629",

language = "English",

volume = "53",

pages = "8411--8415",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "32",

}

TY - JOUR

T1 - Direct asymmetric mannich-type reaction of α-isocyanoacetates with ketimines using cinchona alkaloid/copper(II) catalysts

AU - Hayashi, Masashi

AU - Iwanaga, Masaru

AU - Shiomi, Noriyuki

AU - Nakane, Daisuke

AU - Masuda, Hideki

AU - Nakamura, Shuichi

PY - 2014/8/4

Y1 - 2014/8/4

N2 - The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.

AB - The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.

KW - Lewis acid

KW - alkaloids

KW - asymmetric synthesis

KW - copper

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/84905371193

U2 - 10.1002/anie.201404629

DO - 10.1002/anie.201404629

M3 - Article

C2 - 24985050

AN - SCOPUS:84905371193

SN - 1433-7851

VL - 53

SP - 8411

EP - 8415

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

Direct asymmetric mannich-type reaction of α-isocyanoacetates with ketimines using cinchona alkaloid/copper(II) catalysts

抄録

文献へのアクセス

他のファイルとリンク

フィンガープリント

引用スタイル