Premium
Stereoselective Synthesis of Alcohols, L . Synthesis and Conformational Studies of 1,5‐Dioxa‐ cis ‐decalin
Author(s) -
Hoffmann Reinhard W.,
Münster Ingo
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970614
Subject(s) - decalin , chemistry , tetrahydropyran , intramolecular force , stereoselectivity , acetonitrile , ring (chemistry) , lithium (medication) , stereochemistry , derivative (finance) , conformational isomerism , medicinal chemistry , organic chemistry , catalysis , molecule , medicine , financial economics , economics , endocrinology
cis ‐2‐Vinyltetrahydropyran‐3‐ol ( 6 ) is accessible by a selective intramolecular allylboration reaction. Compound 6 was converted into 1,4‐dioxa‐ cis ‐decaline ( 4 ) and cis‐syn‐cis ‐perhydrotrioxaanthracene 32 ; heterocycles with fused tetrahydropyran rings. These ring systems populate predominantly the conformation in which the oxygen atoms are in a gauche arrangement. The tricycle 31 is a rigid derivative of 14‐crown‐3 and, as in the case of 12‐crown‐3, it forms complexes with lithium ions in acetonitrile.