Practical and Highly Stereoselective Synthesis of Trisubstituted (E)-α,β-Unsaturated Esters

Autor:	Sumire Izumiya, Naoto Kojima, Minoru Ozeki, Honoka Egawa, Akiko Kuse, Masayuki Yamashita, Shinzo Hosoi, Kenji Arimitsu, Takuya Miura, Manabu Node, Tetsuya Kajimoto, Daichi Nakashima, Narumi Yasuda, Hideki Mizutani, Hiroki Iwasaki, Toshiki Takano
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Elimination reaction chemistry Aldol reaction Organic reaction Acetylation Organic Chemistry Hydroxy group Organic chemistry Stereoselectivity Selectivity Catalysis E1cB-elimination reaction
Zdroj:	Synthesis. 47:3392-3402
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0034-1378786
Popis:	Trisubstituted (E)-α,β-unsaturated esters bearing various substituents were synthesized with high geometrical selectivity by using three reactions: an aldol reaction, acetylation of the hydroxy group at the β-position, and an E1cB reaction induced by 1,8-diazabicyclo[5.4.0]undec-7-ene. The method does not require separation of the diastereoisomeric mixture of β-hydroxy ester intermediates before the E1cB reaction, and is usable for gram-scale syntheses of trisubstituted (E)-α,β-unsaturated esters.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7d8a148d8a00e19237883c86a71c6628 https://doi.org/10.1055/s-0034-1378786 Zobrazit plný text záznamu