Synthesis 2013; 45(15): 2134-2136
DOI: 10.1055/s-0033-1338479
special topic
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Multicatalytic Synthesis of α-Benzyl-β-hydroxyindan-1-ones

Takeyuki Suzuki*
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan   Fax: +81(6)68798519   suzuki-t@sanken.osaka-u.ac.jp
,
Yuka Ishizaka
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan   Fax: +81(6)68798519   suzuki-t@sanken.osaka-u.ac.jp
,
Kazem Ghozati
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan   Fax: +81(6)68798519   suzuki-t@sanken.osaka-u.ac.jp
,
Da-Yang Zhou
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan   Fax: +81(6)68798519   suzuki-t@sanken.osaka-u.ac.jp
,
Kaori Asano
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan   Fax: +81(6)68798519   suzuki-t@sanken.osaka-u.ac.jp
,
Hiroaki Sasai
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan   Fax: +81(6)68798519   suzuki-t@sanken.osaka-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 11 March 2013

Accepted after revision: 16 April 2013

Publication Date:
08 May 2013 (online)

Abstract

Asymmetric tandem coupling of meso-diols with aldehydes was achieved by using a chiral iridium catalyst. This tandem reaction consists of oxidative desymmetrization of the meso-diol, aldol condensation with an aldehyde, and reduction of the enone intermediate. A one-pot method using an excess of a hydrogen donor gave α-benzyl-β-hydroxyindan-1-ones in up to 94% ee and 88% yield. An asymmetric hydrogen autotransfer method in the absence of an additional hydrogen donor gave the desired benzyl ketone in 92% ee.

Supporting Information

 
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