The preparation of nonracemic secondary alpha-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols.
[reaction: see text] Chiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl(2). Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.
Papillon
Julien P N
JP
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Taylor
Richard J K
RJ
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000438:Alcohols / Q000138:chemical synthesis*; D000818:Animals; D002219:Carbamates; D002384:Catalysis; D001517:Coleoptera; D003300:Copper; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D012724:Sex Attractants / Q000138:chemical synthesis; D013237:Stereoisomerism; D015032:Zinc
D000438:Alcohols; D002219:Carbamates; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D012724:Sex Attractants; C117438:japonilure; D003300:Copper; D015032:Zinc; D015107:4-Butyrolactone