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Novel binuclear chiral zirconium catalysts used in enantioselective strecker reactions

Corresponding Author

Shū Kobayashi

[email protected]

Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Tokyo, Japan

Graduate School of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, JapanSearch for more papers by this author

Haruro Ishitani,

Haruro Ishitani

Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Tokyo, Japan

Search for more papers by this author

Shū Kobayashi,

Corresponding Author

Shū Kobayashi

[email protected]

Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Tokyo, Japan

Graduate School of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, JapanSearch for more papers by this author

Haruro Ishitani,

Haruro Ishitani

Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Tokyo, Japan

Search for more papers by this author

First published: 19 May 2000

https://doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<540::AID-CHIR42>3.0.CO;2-P

Citations: 53

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Abstract

A novel binuclear chiral zirconium catalyst was successfully used in enantioselective Strecker reactions. The catalyst was readily prepared from zirconium t-butoxide (Zr(OtBu)4), (R)-6,6′-dibromo-1,1′-bi-2-naphthol ((R)-6-Br-BINOL), and (R)-3,3′-dibromo-1,1′-bi-2-naphthol ((R)-3-Br-BINOL) to form unique binuclear structure. It was revealed that a combination of (R)-6-Br-BINOL and (R)-3-Br-BINOL was essential in these asymmetric reactions and that much lower selectivities were obtained by using other combinations. Two-component (an imine and hydrogen cyanide (HCN)) and three-component (an aldehyde, an amine, and HCN) Strecker reactions proceeded smoothly in the presence of a catalytic amount of the chiral zirconium catalyst to afford the corresponding α-amino nitrile derivatives in high yields with high enantioselectivities. Chirality 12:540–543, 2000. © 2000 Wiley-Liss, Inc.

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Volume12, Issue5-6

SPECIAL COMMEMORATIVE ISSUE HONORING PROFESSOR RYOJI NOYORI

2000

Pages 540-543

Novel binuclear chiral zirconium catalysts used in enantioselective strecker reactions

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Novel binuclear chiral zirconium catalysts used in enantioselective strecker reactions

Abstract

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