Chemistry of Unique Chiral Olefins. 3. Synthesis and Absolute Stereochemistry of trans- and cis-1,1',2,2',3,3',4,4'- Octahydro-3,3'-dimethyl-4,4'-biphenanthrylidenes

摘要

Unique chiral olefins with two methyl groups as the internal reference of absolute stereochemistry, (3R, 3'R)- (P,P)-(E)-(-)-1,1',2,2',3,3',4,4'- Octahydro-3,3'-dimethyl-4,4'-biphenanthrylidenes (3) and its (3R, 3'R)-(P,P)-(Z)-isomer (4), were synthesized in optically pure form starting from (3R,4R)-(+)-tetrahydro-3-methyl-4-phenanthrenol (11), which was obtained by the enantioresolution using a novel chiral auxiliary of dichlorophthalic acid amide (14).