Enantioselective synthesis of spiropentanes from hydroxymethylallenes.
[reaction: see text]. Hydroxymethylallenes are efficiently converted to the corresponding spiropentanes in high yields and enantiomeric ratios upon treatment with Zn(CH2I)2 and dioxaborolane ligand 1. The reaction also proceeds with complete diastereocontrol. The application of this methodology to the synthesis of spiropentaneacetic acid is also presented.
Charette
A B
AB
Département de Chimie, Université de Montréal, P.O. 6128 Station Downtown, Montréal, Québec, Canada H3C 3J7. andre.charette@umontreal.ca
Jolicoeur
E
E
Bydlinski
G A
GA
D000466:Alkadienes / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D044943:Fatty Acid Desaturases / Q000037:antagonists & inhibitors; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000466:Alkadienes; D004791:Enzyme Inhibitors; D013141:Spiro Compounds; C071537:spiropentaneacetic acid; C025947:propadiene; D044943:Fatty Acid Desaturases