Synthesis, circular dichroism and absolute stereochemistry of 1,1 ',2,2 ',3,3 ',4,4 '-octahydro-3,3 '-dimethyl-4,4 '-biphenanthryl

Authors
Koumura, N Osawa, S Harada, N
Citation
N. Koumura et al., Synthesis, circular dichroism and absolute stereochemistry of 1,1 ',2,2 ',3,3 ',4,4 '-octahydro-3,3 '-dimethyl-4,4 '-biphenanthryl, ENANTIOMER, 5(1), 2000, pp. 129-133
Citations number
21
Categorie Soggetti
Chemistry
Journal title
ENANTIOMER
ISSN journal
10242430 → ACNP
Volume
5
Issue
1
Year of publication
2000
Pages
129 - 133
Database
ISI
SICI code
1024-2430(2000)5:1<129:SCDAAS>2.0.ZU;2-U
Abstract
In the course of synthetic studies of chiral olefins, (3R,3'R)-(P, P)-(E)-( -)-1,1 ',2,2',3,3',4,4'-octahydro-3,3'-dimethyl-4,4'-biphenanthrylidene (1) and its (3R, 3'R)-(P, P)-(Z)-(+)-isomer (2), chiral (3R,3'R,4R,4'R)-(-)1,1 ',2,2',3,3',4,4'-octahydro-3,3'-dimethyl-4,4'-biphenanthryl(3) was obtained as a by-product in the McMurry reaction of (3R)-(-)-2,3-dihydro-3-methyl-4 (1H)-phenanthrenone (4). The relative and absolute stereostructures of (-)- 3 were fully determined by NMR, X-ray crystallographic, and CD spectral ana lyses.