Regioselective Pinacol Rearrangement of Unsymmetrical Cyclobutane-1,2-diols

Autor:	Daniel Uguen, Sylvain Pira, Vincent Gembus, Lydia Karmazin
Rok vydání:	2018
Předmět:	010405 organic chemistry Regioselectivity General Chemistry 010402 general chemistry Pinacol rearrangement 01 natural sciences Medicinal chemistry Prenol 0104 chemical sciences Sulfone Cyclobutane chemistry.chemical_compound chemistry Reagent Derivative (chemistry) Cis–trans isomerism
Zdroj:	Bulletin of the Chemical Society of Japan. 91:319-336
ISSN:	1348-0634 0009-2673
Popis:	Hydroxy-sulfone 34b, prepared as a mixture of trans and cis isomers by condensing the O-silyl derivative 18c of 2-hydroxy-2-methyl-cyclobutanone 18b — the Norrish II photocyclisation product of 2,3-pentanedione 21 — and methyl phenyl sulfone 33 was found to rearrange selectively either to the cyclopropanic β-ketosulfone 37 or the isomeric methyl ketone 38 by using, respectively, the tosyl fluoride/DBU and the DAST reagent. The potential of this methodology has been illustrated by a synthesis of phytal 1 from geranylacetone 46, and by the preparation from 3,4-hexanedione 51 and prenol 56 — via the cyclopropanic β-ketosulfone 54 (X-ray) — of an advanced fragment of the juvenile hormone molecule 59.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::799aa90f09da93c74571a4d958b2ec17 https://doi.org/10.1246/bcsj.20170335 Zobrazit plný text záznamu