Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 14, Pages 5764-5767Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050684z
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A formal total synthesis of the sex attractant of male dried bean beetle, methyl (RE)-(-)-tetradeca-2,4,5-trienoate, was achieved by a new efficient route utilizing the Pd-catalyzed asymmetric allene synthesis reaction. It was found that the atropisomeric biaryl bisphosphine (R)-segphos showed better enantioselectivity than (R)-binap in the Pd-catalyzed reaction for preparing alkyl-substituted axially chiral allenes.
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