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- Title
The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis.
- Authors
Saigitbatalova, Elena Sh.; Latypova, Liliya Z.; Zagidullin, Almaz A.; Kurbangalieva, Almira R.; Gridnev, Ilya D.
- Abstract
A previously unknown reduction of carbonyl compounds with dicyclopentylzinc is reported. Aldehydes react in mild conditions yielding corresponding primary alcohols and cyclopentene. Although cyclohexanone and acetophenone are inert to dicyclopentylzinc, a variety of heterocyclic ketones reacted readily, yielding reasonable to high yields of corresponding secondary alcohols. When the reaction was catalyzed with (–)-(1R,2S)-ephedrine, 3-acetylpyridine (10) resulted in a high yield of (S)-1-(pyridin-3-yl)ethanol (19) with >99% ee. 5-Acetyl-2-bromopyridine (11) also provided the corresponding optically active alcohol 20, albeit with a much lower optical yield. When 10% of 19 with 92% ee was used as an autocatalyst, 55% yield of the same compound was obtained, with 95% ee and 96% ee in two independent experiments. A three-stage reaction sequence starting from "no chirality" reaction yielded 19 with 6% ee. Thus, amplifying autocatalysis was detected in the reaction of ketone 10 with dicylopentylzinc.
- Subjects
CARBONYL compounds; AUTOCATALYSIS; KETONES; CYCLOHEXANONES; ALCOHOL; CHEMICAL yield; ETHANOL
- Publication
International Journal of Molecular Sciences, 2023, Vol 24, Issue 23, p17048
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms242317048