Synlett 2013; 24(5): 630-634
DOI: 10.1055/s-0032-1318301
letter
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Preparation of New N,N-Dialkyl-2-amino-1,1,2-triphenylethanol Catalysts and a Kinetic Resolution in the Addition of Diethylzinc to Flavene-3-carbaldehydes

Seock Yong Kang
Department of Chemistry and KFnSC, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 143-701, Korea   Fax: +82(2)34365382   eMail: parkyong@konkuk.ac.kr
,
Jinho Baek
Department of Chemistry and KFnSC, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 143-701, Korea   Fax: +82(2)34365382   eMail: parkyong@konkuk.ac.kr
,
Yi Kyung Ko
Department of Chemistry and KFnSC, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 143-701, Korea   Fax: +82(2)34365382   eMail: parkyong@konkuk.ac.kr
,
Chan Im
Department of Chemistry and KFnSC, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 143-701, Korea   Fax: +82(2)34365382   eMail: parkyong@konkuk.ac.kr
,
Yong Sun Park*
Department of Chemistry and KFnSC, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 143-701, Korea   Fax: +82(2)34365382   eMail: parkyong@konkuk.ac.kr
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Publikationsverlauf

Received: 18. Dezember 2012

Accepted after revision: 01. Februar 2013

Publikationsdatum:
25. Februar 2013 (online)


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Abstract

Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenyl­ethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N-substituents of the catalysts led us to identify N-methyl-N-(S)-1-phenyl­ethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3-carbaldehydes with the chiral catalyst.

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