Volume 12, Issue 5-6 pp. 352-359

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Synthesis of axially chiral benzamides utilizing tricarbonyl(arene)chromium complexes

Hiroshige Koide,

Hiroshige Koide

Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka, Japan

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Motokazu Uemura,

Corresponding Author

Motokazu Uemura

[email protected]

Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka, Japan

Reserach Institute for Advanced Science and Technology, Osaka Prefecture University, Sakai, Osaka, Japan

Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, JapanSearch for more papers by this author

Hiroshige Koide,

Hiroshige Koide

Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka, Japan

Search for more papers by this author

Motokazu Uemura,

Corresponding Author

Motokazu Uemura

[email protected]

Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka, Japan

Reserach Institute for Advanced Science and Technology, Osaka Prefecture University, Sakai, Osaka, Japan

Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, JapanSearch for more papers by this author

First published: 19 May 2000

https://doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<352::AID-CHIR9>3.0.CO;2-P

Citations: 9

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Abstract

Axially chiral N,N-diethyl 2,6-disubstituted benzamides were stereo-selectively prepared utilizing planar chiral (arene)chromium complexes as an enantiomerically active form by following two methods. Ortho-lithiation of the enantiomerically pure planar chiral tricarbonyl(N,N-diethyl 2-methylbenzamide)chromium complex followed by electrophilic quenching gave axially chiral 2-methyl-6-substituted N,N-diethyl benzamide chromium complexes. Photo-oxidative demetalation produced the chromium-free axially chiral benzamides as optically active compounds. An alternative method for the preparation of axial chiral benzamides is an enantioselective lithiation at the benzylic methyl of meso tricarbonyl(N,N-diethyl 2,6-dimethylbenzamide)chromium with appropriate chiral lithium amide base followed by quenching with alkyl halides. Chirality 12:352–359, 2000. © 2000 Wiley-Liss, Inc.

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Volume12, Issue5-6

SPECIAL COMMEMORATIVE ISSUE HONORING PROFESSOR RYOJI NOYORI

2000

Pages 352-359

Synthesis of axially chiral benzamides utilizing tricarbonyl(arene)chromium complexes

Abstract

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Synthesis of axially chiral benzamides utilizing tricarbonyl(arene)chromium complexes

Abstract

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