{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,14]],"date-time":"2026-05-14T18:32:55Z","timestamp":1778783575640,"version":"3.51.4"},"reference-count":49,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["22-13-00275"],"award-info":[{"award-number":["22-13-00275"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>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 (\u2013)-(1R,2S)-ephedrine, 3-acetylpyridine (10) resulted in a high yield of (S)-1-(pyridin-3-yl)ethanol (19) with &gt;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 \u201cno chirality\u201d reaction yielded 19 with 6% ee. Thus, amplifying autocatalysis was detected in the reaction of ketone 10 with dicylopentylzinc.<\/jats:p>","DOI":"10.3390\/ijms242317048","type":"journal-article","created":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T10:39:48Z","timestamp":1701427188000},"page":"17048","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2392-7912","authenticated-orcid":false,"given":"Elena Sh.","family":"Saigitbatalova","sequence":"first","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Liliya Z.","family":"Latypova","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3125-7506","authenticated-orcid":false,"given":"Almaz A.","family":"Zagidullin","sequence":"additional","affiliation":[{"name":"A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov Street, 420088 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2436-7427","authenticated-orcid":false,"given":"Almira R.","family":"Kurbangalieva","sequence":"additional","affiliation":[{"name":"Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6711-9036","authenticated-orcid":false,"given":"Ilya D.","family":"Gridnev","sequence":"additional","affiliation":[{"name":"N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prosp. 47, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1038\/378767a0","article-title":"Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule","volume":"378","author":"Soai","year":"1995","journal-title":"Nature"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1246\/bcsj.77.1063","article-title":"Discovery and development of asymmetric autocatalysis","volume":"77","author":"Soai","year":"2004","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1135\/cccc20030849","article-title":"Absolute asymmetric synthesis: A commentary","volume":"68","author":"Mislow","year":"2003","journal-title":"Collect. Czech. Chem. 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