Stereochemistry of 11-Hydroxy-1,3,5,7,11-pentamethyl-2,4,6,8-tetraoxatricyclo[3.3.3.0(3,7)]undecan-9-one and Related Diols

Autor:	Ioanna Alexandropoulou, Asmita V. Patel, Trevor A. Crabb
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Oxygen atom Chemistry Stereochemistry Organic Chemistry Drug Discovery Substituent Ring (chemistry) Biochemistry Conformational isomerism
Zdroj:	Tetrahedron. 56:10005-10009
ISSN:	0040-4020
Popis:	11-Hydroxy-1,3,5,7,11-pentamethyl-2,4,6,8-tetraoxatricyclo[3.3.3.0 (3,7) ]undecan-9-one adopts an equilibrium (in CD 2 CI 2 at −90°C) between ca. 68% of the conformer with a pseudo-axial C-11 methyl substituent and ca. 32% of the alternative pseudo-equatorially substituted conformer. The derived cis -9,11-diol, cis -9,11-dimethyldiol and cis -9-phenyl-11-methyldiol adopt conformational equilibria heavily biased towards the diaxial OH conformations which are stabilised by internal H-bonds involving the dioxolan ring oxygen atoms.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::80ee162b6a6f29dc2c35f86925601103 https://doi.org/10.1016/s0040-4020(00)00952-2 Zobrazit plný text záznamu Full Text from ScienceDirect