Regio- and Stereoselective Approach to 1,4-Ditertiary Carbinols from Dimethyl Tartrate

Autor:	Alexander Roller, Michael Widhalm, Tuvshinjargal Budragchaa
Rok vydání:	2012
Předmět:	chemistry.chemical_compound Nucleophilic addition chemistry Yield (chemistry) Organic Chemistry Grignard reaction Tartaric acid Organic chemistry Regioselectivity Stereoselectivity Tartrate Catalysis
Zdroj:	Synthesis. 44:3238-3250
ISSN:	1437-210X 0039-7881
Popis:	A rational strategy for accessing tetrahydroxy compounds in predictable stereoselective fashion from di-O-benzyl protected tartrate is presented. Up to four different aromatic, aliphatic, and vinyl substituents could be stepwise introduced at C1 and C4. This is exemplified in an economic preparation of eight dihydroxy compounds from natural tartaric acid in six steps and 19–59% overall yield. A final deprotection step afforded the corresponding tetrahydroxy compounds in good yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::eb1aff0992b3c35f91b386b05811bfc7 https://doi.org/10.1055/s-0032-1317168 Zobrazit plný text záznamu