Chemoselective reduction of α,β-unsaturated ketones to allylic alcohols under catalyst-free conditions

Author:

Jian Kaixia1,Li Bingnan1,Zhu Shuxian1,Xuan Qingqing1,Song Qiuling1234ORCID

Affiliation:

1. Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian, 361021, China

2. Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, Guangdong, China

3. State Key Laboratory of Organometallic Chemistry and Key Laboratory of Organo-fluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

4. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007

Abstract

A strategy of chemoselective reduction of α, β-unsaturated ketones was developed in our group. H3N·BH3 would prefer to coordinate with CO bond, forming six-membered ring, and ketones were hydrogenated via concerted double-hydrogen-transfer process.

Funder

National Natural Science Foundation of China

Guangdong Provincial Key Laboratory Of Catalysis

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Reference65 articles.

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2. T.Katsuki , in ComprehensiVe Asymmetric Catalysis , ed. E. N. Jacobsen , A. Pfaltz and H. Yamamoto , Springer , Berlin , 1999 , Vol. 2 , p. 621

3. J.Tsuji , Palladium Reagents and Catalysis , VCH , Chichester , 1997 , ch. 4

4. Ruthenium-NHC-Catalyzed Asymmetric Hydrogenation of Flavones and Chromones: General Access to Enantiomerically Enriched Flavanones, Flavanols, Chromanones, and Chromanols

5. Highly Enantioselective Synthesis of Optically Active Ketones by Iridium-Catalyzed Asymmetric Hydrogenation

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