Remarkable Differences in Reactivity between Benzothiazoline and Hantzsch Ester as a Hydrogen Donor in Chiral Phosphoric Acid Catalyzed Asymmetric Reductive Amination of Ketones
- Authors
- Kim, Kyung-Hee; Akiyama, Takahiko; Cheon, Cheol-Hong
- Issue Date
- 20-1월-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- benzothiazolines; chiral phosphoric acid catalysis; enantioselective reductive amination; Hantzsch ester; organic hydrogen donor
- Citation
- CHEMISTRY-AN ASIAN JOURNAL, v.11, no.2, pp.274 - 279
- Indexed
- SCIE
SCOPUS
- Journal Title
- CHEMISTRY-AN ASIAN JOURNAL
- Volume
- 11
- Number
- 2
- Start Page
- 274
- End Page
- 279
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/89774
- DOI
- 10.1002/asia.201501020
- ISSN
- 1861-4728
- Abstract
- Described herein are differences in behavior between a Hantzsch ester and a benzothiazoline as hydrogen donors in the chiral phosphoric acid catalyzed asymmetric reductive amination of ketones with p-anisidine. The asymmetric reductive amination of ketones with a Hantzsch ester as a hydrogen donor provided the corresponding chiral amines exclusively, regardless of the structures of the ketones, whereas a similar transformation with a benzothiazoline provided chiral amines and p-methoxyphenyl-protected primary amines in variable yields, depending on the structures of both the ketones and benzothiazolines. Because a benzothiazoline has an N,S-acetal moiety that is vulnerable to p-anisidine, the primary amine can be formed through transimination of the benzothiazoline with p-anisidine followed by reduction of the resulting aldimine with remaining benzothiazoline.
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