Catalytic enantioselective synthesis of vicinal dialkyl arrays.
With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.
van Zijl
Anthoni W
AW
Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands.
Szymanski
Wiktor
W
López
Ferrnando
F
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000818:Animals; D001000:Ants; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D004952:Esters; D007659:Ketones; D010675:Pheromones; D013438:Sulfhydryl Compounds; C532716:faranal; C089338:lasiol; D003300:Copper