Počet záznamů: 1
One and Two-Carbon Homologation of Primary and Secondary Alcohols to Corresponding Carboxylic Esters Using β-Carbonyl BT Sulfones as a Common Intermediate
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SYSNO ASEP 0489842 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název One and Two-Carbon Homologation of Primary and Secondary Alcohols to Corresponding Carboxylic Esters Using β-Carbonyl BT Sulfones as a Common Intermediate Tvůrce(i) Bon, D.J.Y.D. (CZ)
Kováč, O. (CZ)
Ferugová, V. (CZ)
Zálešák, F. (CZ)
Pospíšil, Jiří (UEB-Q) ORCID, RID, SAICelkový počet autorů 5 Zdroj.dok. Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 83, č. 9 (2018), s. 4990-5001Poč.str. 12 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova ALPHA-DIAZOCARBONYL COMPOUNDS ; RADICAL-MEDIATED CLEAVAGE ; STEREOSELECTIVE ALKYLATION Vědní obor RIV EB - Genetika a molekulární biologie Obor OECD Organic chemistry CEP LO1304 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy LO1204 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UEB-Q - RVO:61389030 UT WOS 000431726800009 EID SCOPUS 85046624051 DOI 10.1021/acs.joc.8b00112 Anotace Herein we report the efficient one- and two-carbon homologation of 1° and 2° alcohols to their corresponding homologated esters via the Mitsunobu reaction using β-carbonyl benzothiazole (BT) sulfone intermediates. The one-carbon homologation approach uses standard Mitsunobu C-S bond formation, oxidation and subsequent alkylation, while the two-carbon homologation uses a less common C-C bond forming Mitsunobu reaction. In this latter case, the use of β-BT sulfone bearing esters lowers the pK a sufficiently enough for the substrate to be used as a carbon-based nucleophile and deliver the homologated β-BT sulfone ester, and this superfluous sulfone group can then be cleaved. In this paper we describe several methods for the effective desulfonylation of BT sulfones and have developed methodology for one-pot alkylation-desulfonylation sequences. As such, overall, a one-carbon homologation sequence can be achieved in a two-pot (four step) procedure and the two-carbon homologation in a two-pot (three step) procedure (three-pot, four step when C-acid synthesis is included). This methodology has been applied to a wide variety of functionality (esters, silyl ethers, benzyls, heteroaryls, ketones, olefins and alkynes) and are all tolerated well providing good to very good overall yields. The power of our method was demonstrated in site-selective ingenol C20 allylic alcohol two-carbon homologation. Pracoviště Ústav experimentální botaniky Kontakt David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Rok sběru 2019
Počet záznamů: 1