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

Department of Chemistry

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

106 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8411-8415
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	32
DOIs	https://doi.org/10.1002/anie.201404629
Publication status	Published - 4 Aug 2014

Keywords

Lewis acid
alkaloids
asymmetric synthesis
copper
organocatalysis

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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.",

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

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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

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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

Abstract

Keywords

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