Stereoselective 1,4-Addition of Primary Alcohols to γ-Alkoxy-α,β-unsaturated Esters

Autor:	Yuta Takayanagi, Saki Inatomi, Hiroyuki Yamakoshi, Akinori Toita, Seiichi Nakamura, Kento Watanabe
Rok vydání:	2020
Předmět:	chemistry.chemical_compound Primary (chemistry) Nucleophile Chemistry Sodium Organic Chemistry Acetal Alkoxy group Organic chemistry chemistry.chemical_element Stereoselectivity Glycerol Derivatives Catalysis
Zdroj:	Synthesis. 53:161-174
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0040-1707274
Popis:	The scope and limitations of the diastereoselective 1,4-addition reaction of primary alcohols to γ-alkoxy-α,β-unsaturated esters were investigated. We found that a variety of sodium alkoxides, generated from the corresponding primary alcohols with NaH, underwent 1,4-addition reactions with (E)-enoates in CH2Cl2 at –23 °C to give β-alkoxy esters in modest yields with good to excellent syn-selectivity, whereas stereoselectivity was not observed with the use of glycerol derivatives as nucleophiles. Cyclic acetal protection was found to play a pivotal role for the reaction to proceed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2e66fae262112d2fa208d9fd633544a0 https://doi.org/10.1055/s-0040-1707274 Zobrazit plný text záznamu