Asymmetric Hydrogenation of Heterocyclic Ketone-Derived Hydrazones

N. Haddad; B. Qu; S. Rodriguez; L. van der Veen; D. C. Reeves; N. C. Gonnella; H. Lee; N. Grinberg; S. L. Ma; D. Krishnamurthy; T. Wunberg; C. H. Senanayake

doi:10.1055/s-0030-1261067

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Synfacts 2011(10): 1085-1085
DOI: 10.1055/s-0030-1261067

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Asymmetric Hydrogenation of Heterocyclic Ketone-Derived Hydrazones

Contributor(s): Hisashi Yamamoto, Jiajing Tan
N. Haddad*, B. Qu, S. Rodriguez, L. van der Veen, D. C. Reeves, N. C. Gonnella, H. Lee, N. Grinberg, S. L. Ma, D. Krishnamurthy, T. Wunberg, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Inc. Ridgefield, USA and Boehringer Ingelheim RCV GmbH & Co. KG, Vienna, Austria

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Publication History

Publication Date:
20 September 2011 (online)

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Significance

The authors reported a highly practical protocol for the enantioselective hydrogenation of five- or six-membered heterocyclic ketone derived hydrazones. The corresponding products can be obtained with up to 85% enantioselectivity, which can be easily improved to 99% by simple crystallization.