Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.
A highly enantioselective method for catalytic reductive coupling of alkynes and aldehydes is described. Allylic alcohols are afforded with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process is complementary to existing methods of enantioselective alpha-hydroxy ketone synthesis.
Miller
Karen M
KM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Huang
Wei-Sheng
WS
Jamison
Timothy F
TF
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000480:Alkynes; D000498:Allyl Compounds; D007659:Ketones